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Richmond vacation rentals

We found 814 vacation rentals — enter your dates for availability

Discover a selection of 18 homes and other vacation rentals in Richmond that are perfect for your trip. Whether you're going on vacation with family or friends, vacation homes have the amenities you expect for your stay, which might include a pool and a washer and dryer. No matter what you're looking for, you'll find a rental that has what everyone needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Richmond

Showing deals for:Jun 5 - Jun 12

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10 out of 10, Exceptional, (14 reviews)
Exceptional
(14 reviews)

Best of the Berkshires & Hudson Valley

Canaan

9% off
Price is $506
$3,544 for 7 nights
All fees included
Best of the Berkshires & Hudson Valley

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Find out more about Richmond

Why visit Richmond

  • Outdoor Adventures: Enjoy skiing in the winter and hiking in the summer, making Richmond a year-round destination for adventure seekers.
  • Scenic Nature Preserves: Experience serene lakes and beautiful landscapes that offer peaceful escapes and family-friendly excursions.
  • Historic Attractions: Discover charming historic houses that showcase the local culture and history, perfect for family outings.
  • Diverse Accommodations: Choose from a variety of vacation rentals, including private homes, condos, and cozy cottages for a memorable stay.
  • Nearby Exploration: Venture into neighboring cities for romantic vibes and budget-friendly options, enhancing your vacation experience.

Popular types of accommodation in Richmond

If you're exploring vacation rentals in Richmond, you're in for a treat. The most sought-after options include houses, condos, and charming cottages. Whether you're searching for the perfect apartment or a cozy house rental, our Richmond rent program offers a variety of ideal apartment rentals to suit your needs. Discover the perfect accommodation that will make your stay memorable and enjoyable.

  • Houses: The top choice for visitors in Richmond, these spacious homes offer a comfortable and private stay for families, groups, or couples.
  • Condos: A popular option for travelers seeking modern amenities and convenient locations, perfect for a relaxing getaway.
  • Cottages: Charming and cozy, these quaint rentals provide a unique experience amidst the scenic beauty of Richmond.
  • Apartments: Ideal for those looking for a home-away-from-home feel, apartments combine comfort with accessibility.
  • Cabins: A favorite for nature lovers, these rustic retreats offer a peaceful escape in the great outdoors.**

Top attractions near Richmond

Richmond, Massachusetts, is an ideal destination for adventure seekers and outdoor enthusiasts. With its historic houses, serene lakes, and nature preserves, the area offers a variety of attractions that appeal to those interested in culture and family experiences. Whether you're hitting the slopes or enjoying a peaceful hike, Richmond promises a memorable vacation filled with exciting activities for everyone.

  • National Shrine of the Divine Mercy: Nestled 6 miles from Richmond, this serene shrine offers a peaceful environment for reflection and prayer, featuring beautiful gardens and stunning architecture that embody spiritual tranquility.
  • Norman Rockwell Museum: Located 6 miles away, this art museum celebrates the beloved American illustrator's work, showcasing his iconic paintings and providing insights into his creative process in a charming, cultural setting.
  • The Mount: Just 5 miles from Richmond, this historic house was the home of author Edith Wharton, featuring exquisite gardens and architecture, allowing visitors to explore Wharton's literary legacy and her connection to the Berkshires.

Things to do recommended for couples

Richmond offers a perfect romantic getaway. Enjoy a concert at Tanglewood Music Center, ski together at Bousquet Ski Area, or indulge in wine tasting at Furnace Brook Winery at Hilltop Orchards. Each experience is sure to create lasting memories for you and your partner.

Things to do recommended for families

Your family will love exploring Kennedy Park, a serene recreational area just 5 miles from Richmond, or enjoying the tranquility of Shatford Memorial Park, located 7 miles away. Don't miss the peaceful Fairfield Brook WMA, right in Richmond, perfect for relaxation and outdoor fun.

Things to do recommended for groups

In Richmond, groups can enjoy a captivating performance at Shakespeare and Company, just 5 miles away, shop at Charles H. Baldwin & Sons, 3 miles from town, or hit the greens at Wyndhurst Golf & Club, located 6 miles away for a fun day outdoors.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Richmond

If you're traveling with a group, family, or pets, or if you're seeking extended stays, it's important to prioritize your filters accordingly. Here are some helpful booking tips for using Vrbo.

  • Traveling to Richmond with a group: Think about how many bedrooms you require, as well as features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Richmond with young kids: Traveling with little ones can be a bit challenging. It's important to prioritize their comfort and safety, along with finding suitable amenities like a private pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Richmond: For many families, a vacation isn't truly complete without their furry companion. If you can relate, explore Vrbo listings that welcome pets. Most of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Richmond: If you’re in search of vacation rentals that offer discounts for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay near Richmond

Richmond, Massachusetts offers an ideal getaway for adventure seekers and outdoor enthusiasts. With its mild climate, visitors can enjoy family-friendly excursions and relax in scenic surroundings. Explore nearby cities and neighborhoods to experience romantic vibes and budget-friendly options. Whether you're skiing in the winter or hiking in the summer, Richmond provides a perfect blend of relaxation and adventure for an unforgettable vacation.

  • Lenox: Nestled just 4 miles from Richmond, Lenox is a charming town known for its romantic ambiance and vibrant entertainment scene. Visitors are drawn to its cultural offerings, including music concerts and theater performances. Outdoor enthusiasts can enjoy nearby skiing and breathtaking mountain views. The local landmarks, such as picturesque lakes and event venues, provide ample opportunities for relaxation and recreation. Lenox is perfect for families looking to create lasting memories while indulging in the arts and nature.
  • Pittsfield: Located 8 miles from Richmond, Pittsfield is a hub for adventure seekers and sports enthusiasts. This city offers a wealth of skiing opportunities, with access to multiple ski fields and resorts. Beyond winter sports, visitors can explore scenic lakes and enjoy a fun-filled day at the local waterpark. Pittsfield’s vibrant community and recreational activities make it an exciting destination for those looking to embrace the great outdoors while experiencing the thrill of winter sports.
  • West Stockbridge: Just 3 miles from Richmond, West Stockbridge is a delightful blend of culture and entertainment. The town is known for its captivating theater performances and music concerts, appealing to those seeking a romantic getaway. Visitors can explore stunning lakes and majestic mountains, along with the local art museum that showcases regional talent. West Stockbridge offers a unique experience for tourists eager to immerse themselves in the arts while enjoying a serene atmosphere perfect for relaxation.

Best time to go to Richmond

If you're planning a trip to Richmond, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from July to September, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January22.8°F (-5.1°C)Light RainMostly CloudySlightly LowAverage
February24.6°F (-4.1°C)Light RainMostly CloudyAverageAverage
March32.5°F (0.3°C)Light RainMostly CloudyAverageSlightly Low
April44.2°F (6.8°C)Light RainMostly CloudyAverageSlightly Low
May56.3°F (13.5°C)Light RainMostly SunnyAverageAverage
June64.0°F (17.8°C)Light RainMostly SunnyAverageAverage
July70.3°F (21.3°C)Light RainMostly SunnySlightly HighSlightly High
August68.4°F (20.2°C)Light RainMostly SunnySlightly HighSlightly High
September61.3°F (16.3°C)Light RainMostly SunnySlightly HighAverage
October50.0°F (10.0°C)Light RainMostly SunnyAverageSlightly Low
November37.8°F (3.2°C)Light RainMostly SunnySlightly LowAverage
December29.5°F (-1.4°C)Light RainMostly CloudySlightly LowSlightly High

Booking with Vrbo is a breeze

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can change significantly. Plus, booking a longer stay can often result in substantial savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to refine your search by price, location, and type of vacation rental.

Save more with One Key

When you reserve a qualifying Vrbo for your group getaway, you'll earn OneKeyCash on the full booking amount. It truly benefits you to be the trip organizer. Become a member of our One Key rewards program to unlock exclusive savings and earn OneKeyCash on eligible stays. Sign up today and start reaping the rewards.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board is designed to help you plan your travels more efficiently. You can create new trips, refine your existing plans, or manage your bookings all in one place. Your saved and booked properties are conveniently organized into categories: Potential, Upcoming, or Current Trips. To check out Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Travel to tranquil Richmond

Enjoy the wineries and other features of Richmond. This city's horseback riding, mountain views and restaurants attract many visitors, and its relaxing and welcoming location add to the charm. Are you looking for specific amenities for your getaway? Many of our vacation rentals feature full kitchens and laundry facilities.

Activities and attractions in and around Richmond

Do you want to find attractions to see during your stay? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that Richmond has to offer. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Bousquet Ski Area (5.4 mi / 8.6 km)
  • Wyndhurst Golf & Club (5.5 mi / 8.9 km)
  • Jiminy Peak Mountain Resort (13.2 mi / 21.2 km)
  • Ski Butternut (13.4 mi / 21.5 km)
  • Catamount Ski Area (15.3 mi / 24.7 km)
  • Charles H. Baldwin & Sons (2.7 mi / 4.4 km)

Exploring the natural features in Richmond

Whether you're looking for adventure or just want to appreciate the scenery, Richmond is a great place to get outside. Here are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city center:

  • Queechy Lake (3.4 mi / 5.4 km)
  • The Mount (5 mi / 8.1 km)
  • Berkshire Botanical Garden (5.2 mi / 8.4 km)
  • Naumkeag Museum (6.3 mi / 10.2 km)
  • Goose Pond Reservation (11.1 mi / 17.9 km)
  • Housatonic River (12.1 mi / 19.5 km)

How to get to and around Richmond

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 5.3 mi (8.5 km) from the city center. If you can't find a flight that's convenient for your trip, you might consider flying into Hudson, NY (HCC-Columbia County), which is 18.4 mi (29.7 km) away.

Frequently asked questions

What is the best area to stay in Richmond, Massachusetts, United States of America when booking a vacation rental?
When considering a vacation rental in Richmond, Massachusetts, the area around the scenic Berkshire Mountains is particularly appealing. This neighborhood offers a serene atmosphere with beautiful natural landscapes, making it great for those seeking outdoor adventures. You'll find a variety of properties available, ranging from cozy cabins to charming cottages that cater to different tastes and budgets.

One of the top attractions nearby is the picturesque October Mountain State Forest, where visitors can enjoy hiking, biking, and picnicking amidst stunning views. Additionally, the charming local art scene, highlighted by nearby galleries and workshops, provides an enriching cultural experience.
How much does it cost to rent a vacation home in Richmond?
Prices for vacation rentals in Richmond vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Richmond to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Richmond vacation house rentals?
You can find great discounts on house rentals in Richmond on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Richmond?
For renting a beach house in Richmond, Massachusetts, travelers should consider areas along the scenic shores of the nearby Berkshire region, particularly around the picturesque town of Stockbridge. This area offers a selection of vacation rentals that provide easy access to the beautiful beaches along the Housatonic River. Many properties here come equipped with amenities such as private docks, outdoor decks, and spacious living areas, making them ideal for families or groups looking to enjoy water activities and the natural surroundings.

Another great option is the nearby Lake Buel area, which offers lakeside rentals with stunning views and opportunities for swimming, kayaking, and fishing. These properties often feature amenities like fire pits, outdoor grills, and fully equipped kitchens, superb for preparing meals after a day of fun in the sun. The tranquil environment is complemented by proximity to local attractions such as the Norman Rockwell Museum and Tanglewood Music Center, providing a blend of relaxation and cultural experiences. Find your rental near the beach in Richmond.
Where are the best Richmond ski resort rentals?
For skiing near Richmond, Massachusetts, travelers should explore options in the nearby Berkshire Mountains, particularly around the town of Pittsfield, which is conveniently located close to several ski resorts. One of the most popular destinations is Bousquet Ski Area, a short drive away, where visitors can find a variety of rental properties in Pittsfield that cater to winter sports enthusiasts.

Accommodations in this area often include cozy cabins and vacation homes that come equipped with amenities such as kitchens, fireplaces, and outdoor spaces superb for après-ski relaxation. Many properties also provide easy access to local dining options and grocery stores, making it convenient for families or groups to prepare meals after a day on the slopes.

Additionally, the surrounding Berkshires offer picturesque views and opportunities for outdoor activities beyond skiing, such as snowshoeing and winter hiking. Rentals in nearby towns like Lenox or Great Barrington not only provide proximity to ski areas but also access to cultural attractions like museums, art galleries, and local shops.
What is the most popular type of vacation rental accomodation in Richmond?
In Richmond, vacation houses are the most popular type of accommodation, with about 15 available throughout the area. These properties typically feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups seeking comfort and convenience. Additionally, there are several cottages and apartments scattered around, offering a cozy and homey atmosphere. Cottages often come with charming outdoor spaces, while apartments provide a more compact option for those looking to enjoy the serene surroundings of Richmond.
Are there any family house rentals in Richmond?
In Richmond, Massachusetts, there are some available family-friendly house rentals, with about 14 options to choose from. The area is known for its serene landscapes and proximity to outdoor activities, making it an excellent choice for families. Many of these homes offer spacious living areas, full kitchens for preparing family meals, and outdoor spaces superb for children to play.

Visitors can also enjoy nearby attractions such as the scenic hiking trails in the Berkshires, which provide ample opportunities for exploration. Additionally, the charming town center offers local shops and eateries, enhancing the family experience.
Can I rent a vacation home with a pool or hot tub in Richmond?
In Richmond, Massachusetts, there are several vacation homes available for rent that feature pools and hot tubs, making it a great destination for relaxation and leisure. Travelers can explore properties located in the picturesque Berkshire Mountains, where they can enjoy scenic views and access to outdoor activities. Many of these rentals come equipped with private swimming pools, hot tubs, and spacious outdoor areas for gatherings or family fun. Inside, guests can expect modern amenities such as fully equipped kitchens, comfortable living spaces, and often, cozy fireplaces for cooler evenings.
Can I find long-stay vacation rentals in Richmond?
A long-stay vacation rental in Richmond is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Richmond?
In Richmond, Massachusetts, there are several pet-friendly house rentals available, with approximately 15 options to choose from. Travelers can expect a variety of amenities in these vacation homes, often including spacious interiors, fully equipped kitchens, and outdoor areas such as decks or patios, great for enjoying the serene surroundings. Many properties are well-suited for families or groups, providing a comfortable base for exploring the beautiful Berkshires region.

Additionally, Richmond's proximity to various parks and outdoor activities makes it a great destination for pet owners. Nearby attractions often include hiking trails and natural areas that welcome pets, allowing for plenty of opportunities to enjoy the outdoors with your furry companions.
Are there any remote work vacation rentals in Richmond?
In Richmond, Massachusetts, there are about 20 vacation rentals that cater to remote work needs. Travelers can find accommodations equipped with essential amenities such as high-speed Wi-Fi, dedicated work desks, and comfortable desk chairs, making it easy to stay productive during your stay. Many properties also offer free internet access, ensuring that you can easily connect without any additional costs.

The area offers a peaceful retreat surrounded by nature, making it ideal for those looking to balance work and leisure. With the tranquility of the Berkshires nearby, visitors can enjoy outdoor activities such as hiking and exploring the scenic landscapes after a day of remote work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Richmond vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Richmond with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Richmond?
In Richmond, popular vacation rental amenities include fully equipped kitchens, allowing travelers to prepare their own meals during their stay. Many properties also feature decks or patios, providing outdoor space to relax and enjoy the natural surroundings. Onsite parking is commonly available for guests, adding convenience for those traveling by car.
When is the best time to visit Richmond for a vacation rental?
The best time to book a vacation rental in Richmond is during the peak season from July to September. This vibrant period attracts visitors looking to embrace the warm weather and partake in outdoor activities, including hiking the scenic trails of the nearby Berkshire Mountains and exploring the beautiful landscapes that Richmond has to offer. July stands out as the most popular month, where the town comes alive with events and a lively option, making it an ideal choice for those seeking both adventure and community.

During these summer months, temperatures typically range from the mid-60s to the low 80s Fahrenheit, providing comfortable conditions for outdoor excursions and sightseeing. Richmond's plethora of parks and recreational areas become hotspots for families and nature enthusiasts alike, offering opportunities for picnicking, boating, and enjoying the natural beauty of the region.

For travelers looking for a more budget-friendly experience, consider visiting in December. While this month falls outside the peak season, it offers a unique charm with cozy winter landscapes and fewer crowds, making it superb for those who enjoy a quieter atmosphere and the chance to experience the tranquility of Richmond.

Ultimately, your decision on when to visit Richmond will depend on whether you prefer the bustling energy of summer activities or the peacefulness of winter escapes.
How early should I book a Richmond vacation rental?
Book your Richmond vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Richmond, Massachusetts, United States of America?
In Richmond, Massachusetts, visitors can enjoy a variety of attractions that highlight the area's natural beauty and cultural heritage. The town is located in the picturesque Berkshire Mountains, making it a great base for outdoor activities like hiking and fishing. Nearby, the Pittsfield State Forest offers numerous trails and scenic views, ideal for nature enthusiasts.

For those interested in local history, the Richmond Historical Society provides insights into the town's past, featuring exhibits and artifacts. The nearby town of Lenox is home to the famous Tanglewood Music Center, where visitors can attend concerts during the summer months, making it a popular destination for music lovers.

Additionally, the area is close to the charming town of Stockbridge, where travelers can explore the Norman Rockwell Museum, dedicated to the iconic American painter.
Can I change or cancel my Richmond home rental booking on Vrbo?
To find Richmond vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Richmond vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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