Photo by Caitlin Reese

Richmond holiday lettings

We found 807 holiday rentals — enter your dates for availability

Discover a selection of 19 homes and other holiday rentals in Richmond that are perfect for your trip. Whether you're travelling with a group or just with your pet, holiday homes have the best amenities for hanging out with the people that matter most, including air conditioning and cable TV. No matter what you're looking for, you'll find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Richmond

Showing deals for:27 Mar - 3 Apr

Image gallery for Waterfront Cottage 10 Min From Great Barrington

Property grounds
10 out of 10, Exceptional, (99 reviews)
Exceptional
(99 reviews)

Waterfront Cottage 10 Min From Great Barrington

New Marlborough

8% off
Price is £1,861
for 7 nights, 1 cottage
£266 per night
includes taxes & fees
Waterfront Cottage 10 Min From Great Barrington

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Travel to relaxing Richmond

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

Activities and attractions in and around Richmond

Are you looking for things to do during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that Richmond has to offer. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • 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)
  • Furnace Brook Winery at Hilltop Orchards (1.7 mi / 2.8 km)

Exploring the natural features in Richmond

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Richmond is a great place to get outside. Here are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • 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 centre. If you can't find a flight that's convenient for your trip, you could book a flight to 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 when booking a holiday rental?
When considering a holiday rental in Richmond, Massachusetts, the best area to stay in is the picturesque town centre. This charming neighbourhood offers a delightful blend of natural beauty and easy access to various attractions. You'll find a selection of properties that cater to different tastes, from quaint cottages to modern homes, ensuring a comfortable stay.

One of the top attractions in the area is the beautiful Richmond Pond, superb for outdoor enthusiasts and those looking to unwind by the water. The pond offers opportunities for fishing, kayaking, and enjoying serene walks along its shores. Additionally, the nearby Berkshire Botanical Garden is a wonderful point of interest, showcasing stunning floral displays and beautifully landscaped grounds that are sure to inspire any nature lover.
How much does it cost to rent a holiday home in Richmond?
Prices for holiday 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 holiday 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, travellers should consider the nearby regions of the Berkshires, particularly around areas like Stockbridge and Lenox. While these towns are not directly on the coast, they offer beautiful lakeside options, with properties situated along the shores of places like Stockbridge Bowl. Many of these rentals come equipped with amenities such as private docks, outdoor spaces for barbecuing, and stunning views of the surrounding mountains, making them ideal for those looking to enjoy a serene retreat.
Where are the best Richmond ski resort rentals?
For ski resort rentals near Richmond, Massachusetts, the closest ski areas are located in the nearby Berkshires, particularly in towns like Pittsfield and Lenox. In Pittsfield, travellers can find a variety of rental options, including cosy cabins and chalets that often come with amenities such as wood-burning stoves, fully equipped kitchens, and outdoor spaces for enjoying the picturesque mountain scenery. Many properties are conveniently located within a short drive to the ski areas, making it easy to enjoy a day on the slopes.

In Lenox, known for its charming New England atmosphere, visitors can discover lovely holiday homes and quaint cottages, some of which feature amenities like hot tubs, fire pits, and proximity to local attractions, including the beautiful Tanglewood estate. This area also offers access to several hiking trails for those looking to explore the outdoors beyond skiing.
What is the most popular type of holiday rental accomodation in Richmond?
In Richmond, holiday houses are the most popular rental choice, with around 12 available in the area. These houses typically offer ample space, making them ideal for families or groups, and often come with multiple bedrooms, fully equipped kitchens, and private outdoor areas for relaxation. Additionally, there are several apartments and cottages spread throughout the town, which provide a more compact and cosy alternative. Most of these accommodations feature essential amenities like comfortable living spaces and kitchen facilities, ensuring a pleasant stay.
Are there any family house rentals in Richmond?
In Richmond, Massachusetts, there are numerous family-friendly holiday rentals available—specifically, around 13 properties suited for those travelling with children. The town is surrounded by picturesque landscapes, making it an excellent choice for families seeking both relaxation and outdoor activities. Many of the homes feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces for children to play or enjoy a barbecue.
Can I rent a holiday home with a pool or hot tub in Richmond?
In Richmond, Massachusetts, there are several holiday homes available for rent that feature pools and hot tubs. This quaint town, located in the beautiful Berkshires, provides a serene setting for a relaxing getaway. Many of these properties come with amenities such as outdoor pools, inviting hot tubs, spacious decks, and well-equipped kitchens, superb for both leisure and entertaining.
Can I find long-stay holiday rentals in Richmond?
A long-stay holiday rental in Richmond is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Richmond?
In Richmond, Massachusetts, there are several pet-friendly house rentals available, providing a welcoming environment for travellers with furry companions. Many of these properties come equipped with amenities such as spacious backyards, fully stocked kitchens, and cosy living areas, making them ideal for families or groups looking to enjoy a cozy feel.
Are there any remote work holiday rentals in Richmond?
In Richmond, Massachusetts, there are several remote work-friendly holiday rentals available, with around 16 options to choose from. This picturesque town, set against the backdrop of the Berkshires, offers a tranquil setting superb for those looking to combine work and leisure. Many properties are equipped with essential amenities for remote work, including reliable Wi-Fi, dedicated office spaces, desks, and comfortable desk chairs, ensuring a productive environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Richmond holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Richmond with parking available—perfect for families or travellers 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 rental amenities typically include kitchens, which are essential for self-catering, allowing guests to prepare their own meals. Many properties also feature patios, providing a lovely outdoor space to relax and enjoy the fresh air. Additionally, rentals often come equipped with cookware, dishware, and utensils, ensuring that guests have everything they need for cooking and dining. Microwaves and refrigerators are also common, adding to the convenience of these accommodations.
When is the best time to visit Richmond for a holiday rental?
The peak travel season in Richmond is from July to September, when the area buzzes with activity and visitors flock to enjoy the beautiful summer weather. July is particularly popular, offering warm temperatures averaging around 25°C, making it ideal for outdoor pursuits such as hiking and exploring the stunning landscapes of the Berkshires.

During these months, tourists can take advantage of various local events and festivals that add to the vibrant atmosphere. The lush greenery and abundant sunshine create great conditions for activities like kayaking on local lakes or simply enjoying a picnic in one of Richmond's scenic parks.

For those looking for a more budget-friendly option, December presents a lovely opportunity to visit Richmond. While it's considered the low season, the town transforms into a winter wonderland, and visitors can delight in the tranquillity of the area, making it great for peaceful hikes or cosy evenings by the fire in a holiday rental. Plus, you might find some great deals on accommodations during this quieter month.
How early should I book a Richmond holiday rental?
Book your Richmond holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Richmond home rental booking on Vrbo?
To find Richmond holiday 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 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 travellers 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 cosy cabin or a beach house, 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, 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 organising 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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