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Monterey vacation rentals

We found 530 vacation rentals — enter your dates for availability

Discover a selection of 22 homes and other vacation rentals in Monterey that are perfect for your trip. Vacation homes provide the best amenities for you and your friends, family, or even pets, such as air conditioning and a pool. At the end of the day, you'll find a rental for everyone's needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Monterey

Showing deals for:May 22 - May 29

Image gallery for The Playhouse: 7,000 Sq Ft of Berkshires Modern Luxury & History

Interior
10 out of 10, Exceptional, (245 reviews)
Exceptional
(245 reviews)

The Playhouse: 7,000 Sq Ft of Berkshires Modern Luxury & History

Lee

9% off
Price is $986
$6,900 for 7 nights
All fees included
The Playhouse: 7,000 Sq Ft of Berkshires Modern Luxury & History

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Find out more about Monterey

Why visit Monterey

  • Breathtaking scenery: Experience stunning landscapes and serene lakes perfect for relaxation and outdoor adventures.
  • Historic charm: Explore historic houses and local attractions that showcase the rich cultural heritage of the area.
  • Outdoor activities: Enjoy hiking and exploring nearby state parks, offering both adventure and tranquility.
  • Cozy accommodations: Choose from charming vacation rentals, cottages, and condos for a comfortable stay.
  • Friendly atmosphere: Engage with welcoming locals and discover family-friendly activities throughout the picturesque town.

Popular types of accommodation in Monterey

Wondering what kind of accommodations await you in Monterey? You're in luck. Our most popular options include houses, cozy cottages, and stylish condos. Whether you're looking for beachfront houses or spacious house rentals, Monterey's diverse selection of California vacation rentals ensures you'll find the perfect spot for your getaway. Enjoy the charm and beauty of this coastal gem while experiencing true comfort and convenience.

  • Houses: The top choice for visitors to Monterey, offering spacious and comfortable accommodations perfect for families or groups.
  • Condos: A popular option for those seeking modern amenities and convenient locations, ideal for both short and extended stays.
  • Cottages: These charming retreats provide a cozy atmosphere, perfect for a romantic getaway or a peaceful escape.
  • Apartments: A versatile choice, offering a home-like feel with kitchen facilities for those who prefer to cook.
  • Cabins: A favorite among nature enthusiasts, these rustic lodgings offer a unique experience amidst beautiful surroundings.**

Top attractions near Monterey

Monterey, Massachusetts, is perfect for outdoor and romantic getaways, offering breathtaking scenery and a rich cultural experience. Visitors can explore historic houses, serene lakes, and nearby state parks that provide adventure and relaxation. Don't miss out on attractions like Monterey County and Monterey Bay for a delightful coastal escape. Whether you're seeking tranquility or adventure, Monterey has something for everyone to enjoy.

  • National Shrine of the Divine Mercy: A peaceful place of worship and reflection, this shrine offers a serene atmosphere with beautiful architecture and spiritual vibes, perfect for those seeking a moment of tranquility.
  • Lake Buel: A picturesque lake known for its stunning scenery and outdoor activities, ideal for a romantic day out or a relaxing beach experience surrounded by nature.
  • Norman Rockwell Museum: Celebrating the iconic American artist, this museum showcases Rockwell's beloved illustrations and offers a deep dive into American culture and storytelling through art.

Things to do recommended for couples

For a romantic getaway in Monterey, explore Ski Butternut for an adventurous day on the slopes, savor fine wines at Les Trois Emme Winery, and enjoy captivating performances at Jacob's Pillow. Each destination offers a unique blend of romance, culture, and entertainment to create lasting memories together.

Things to do recommended for families

Your family can explore the serene Tyringham Cobble, only 5 miles from Monterey, perfect for relaxation. Goose Pond Reservation, 7 miles away, offers tranquil nature walks, while Lake Mansfield Park, 8 miles off, is great for picnics and enjoying the outdoors together.

Things to do recommended for groups

Explore the Lee Premium Outlets for shopping and entertainment, hike the scenic Housatonic River Walk for outdoor adventure, or enjoy a performance at the Mahaiwe Performing Arts Center for a taste of local culture. All these activities are conveniently located 8 miles from Monterey.

*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 Monterey

When planning your trip, whether you're traveling with friends, family, pets, or seeking extended stays, be sure to prioritize your filters effectively. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Monterey with a group: Think about how many bedrooms you'll require, as well as any amenities like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Monterey with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with features that are suitable for their age, like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly activities.
  • Taking your pets with you to Monterey: For many, a family vacation wouldn't feel complete without their furry companion by their side. If this resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Monterey: If you’re in search of vacation rentals that offer discounts for month-long stays, 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 features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Monterey

Monterey, Massachusetts, offers a picturesque escape for those seeking outdoor adventures and romantic getaways. With its stunning scenery, visitors can enjoy a relaxing atmosphere filled with friendly locals. Explore nearby towns and neighborhoods for family-friendly activities and serene landscapes. Whether you're looking for cozy vacation rentals or a charming downtown experience, Monterey is the perfect destination for a memorable vacation.

  • Lenox: Located 13 miles from Monterey, Lenox is a charming city known for its rich culture and scenic beauty. Travelers flock here for a blend of entertainment, romance, and family-friendly experiences. The town boasts venues for music concerts and theater, providing a vibrant cultural scene. Outdoor enthusiasts can explore stunning local landmarks such as beautiful lakes and majestic mountains. Whether you're enjoying a romantic evening or a family outing, Lenox offers an inviting atmosphere with a variety of activities, including skiing in the winter months and events at its conference venues.
  • The Berkshires: Just 3 miles from Monterey, The Berkshires is a haven for outdoor adventurers and nature lovers. This picturesque region is known for its breathtaking scenery and opportunities for adventure, including skiing at nearby resorts. With stunning lakes and mountains, it’s the ideal spot for hiking, fishing, and enjoying the great outdoors. The Berkshires also hosts numerous events throughout the year, making it a vibrant destination for visitors seeking both relaxation and excitement in a natural setting.
  • Great Barrington: Great Barrington is a lively city located 8 miles from Monterey, attracting travelers with its adventurous spirit and sports activities. The area is renowned for its exceptional skiing opportunities, including access to ski fields and resorts that cater to all skill levels. Surrounded by picturesque lakes, mountains, and a national state park, Great Barrington offers a perfect blend of outdoor adventure and natural beauty. Whether you’re hitting the slopes or exploring the scenic landscapes, Great Barrington is sure to provide a memorable experience.

Best time to go to Monterey

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

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January23.2°F (-4.9°C)Light RainMostly CloudyAverageAverage
February24.8°F (-4.0°C)Light RainMostly CloudyAverageAverage
March32.5°F (0.3°C)Light RainMostly CloudyAverageSlightly Low
April44.2°F (6.8°C)Light RainMostly CloudyAverageSlightly Low
May55.9°F (13.3°C)Light RainMostly SunnyAverageAverage
June63.7°F (17.6°C)Light RainMostly SunnySlightly HighAverage
July69.8°F (21.0°C)Light RainMostly SunnySlightly HighSlightly High
August67.8°F (19.9°C)Light RainMostly SunnySlightly HighSlightly High
September60.8°F (16.0°C)Light RainMostly SunnyAverageSlightly Low
October49.8°F (9.9°C)Light RainMostly SunnySlightly LowAverage
November37.8°F (3.2°C)Light RainMostly SunnySlightly LowAverage
December29.7°F (-1.3°C)Light RainMostly CloudySlightly LowSlightly High

Booking with Vrbo is simple

Are you hoping to save on your upcoming adventure? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, booking a longer stay can lead to substantial savings. To discover a Vrbo property that aligns with your budget, utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your booking. Being the planner has its perks. By joining our One Key travel rewards program, you can immediately access member discounts and earn OneKeyCash on eligible reservations. Sign up today and begin enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board offers you a convenient way to plan your travels. You can start new trips, pick up right where you left off, or easily view and organize your existing plans. All the properties you've saved or booked are now neatly categorized under Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Why people love visiting beautiful Monterey

The forests, wildlife and parks display a scene truly unique to Monterey. Well known for its hiking, fishing and boating, this scenic city won't disappoint. Whether you're planning a family holiday, romantic stay or friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in Monterey

Are you hoping to find attractions to visit in the city? Venture out of your vacation home and experience everything that makes Monterey a one-of-a-kind vacation spot. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Ski Butternut (5.6 mi / 8.9 km)
  • Otis Ridge (5.8 mi / 9.3 km)
  • Wyndhurst Golf & Club (11.7 mi / 18.8 km)
  • Catamount Ski Area (13.7 mi / 22 km)
  • Bousquet Ski Area (16.7 mi / 26.8 km)
  • Furnace Brook Winery at Hilltop Orchards (17.3 mi / 27.9 km)

Exploring the natural landscape of Monterey

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

  • Lake Buel (3.3 mi / 5.4 km)
  • Tyringham Cobble (5.2 mi / 8.3 km)
  • Goose Pond Reservation (7.3 mi / 11.7 km)
  • Housatonic River (7.7 mi / 12.4 km)
  • Housatonic River Walk (7.7 mi / 12.4 km)
  • Lake Mansfield Park (8.1 mi / 13.1 km)

Transportation to and around Monterey

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 17.5 mi (28.1 km) from the city center. If you can't find a flight that's convenient for your trip, you can also fly into Westfield, MA (BAF-Barnes Municipal), which is 25.3 mi (40.7 km) away.

Frequently asked questions

What is the best area to stay in Monterey, Massachusetts, United States of America when booking a vacation rental?
When looking for the best area to stay in Monterey, Massachusetts, you'll want to consider the charming neighborhood near the waterfront, which offers stunning views and a serene atmosphere. This area is great for those who enjoy outdoor activities, with nearby attractions such as the scenic Lake Garfield, ideal for swimming, kayaking, and picnicking. Additionally, the proximity to the picturesque Berkshires allows for easy access to hiking trails and beautiful fall foliage.

Another appealing option is the neighborhood closer to the town center, where you can immerse yourself in the local culture. Here, you'll find delightful shops, cozy cafes, and art galleries that showcase the area's creativity. Staying in this area also puts you within reach of the historic Monterey Community Center, which often hosts events and gatherings that highlight the town's community spirit.
How much does it cost to rent a vacation home in Monterey?
Prices for vacation rentals in Monterey 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 Monterey 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 Monterey vacation house rentals?
You can find great discounts on house rentals in Monterey 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 Monterey?
For renting a beach house in Monterey, travelers should focus on the picturesque coastline along Cannery Row and the nearby Asilomar State Beach. This area offers a variety of vacation rentals that provide easy access to sandy beaches and stunning ocean views. Many properties in this region come equipped with amenities such as spacious decks for outdoor dining, hot tubs, and fully stocked kitchens, ideal for families or groups looking to enjoy a seaside getaway.

Additionally, the neighborhood around the Monterey Bay Aquarium is a prime location, with charming cottages and modern homes that often feature unique touches like fireplaces and ocean-themed decor. Many rentals include proximity to local attractions like restaurants and shops, making it convenient for guests to explore the vibrant local culture.

The nearby Point Lobos State Natural Reserve also presents opportunities for outdoor enthusiasts, with hiking trails and breathtaking coastal scenery. Rentals in this vicinity often highlight amenities such as outdoor showers and picnic areas, enabling guests to enjoy the natural beauty of the area right at their doorstep.
What is the most popular type of vacation rental accomodation in Monterey?
In Monterey, vacation houses are the most popular type of rental accommodation, with about 19 available in the area. These houses typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and often outdoor spaces like decks or patios, making them ideal for families and groups. In addition to houses, there are several cottages, cabins, and chalets that provide special environments and cozy retreats for travelers seeking a more rustic experience.
Are there any family house rentals in Monterey?
In Monterey, Massachusetts, families will find a variety of vacation homes available—around 24 options throughout the area. The charming coastal town is great for family gatherings, with many properties offering spacious living areas, well-equipped kitchens for family meals, and outdoor spaces for kids to enjoy. Common amenities include Wi-Fi and air conditioning, ensuring a comfortable stay for all.

Nearby, families can explore attractions like the beautiful beaches along the coast, ideal for swimming and beach games, as well as local parks offering picnic areas and playgrounds. The scenic landscape also provides opportunities for hiking and nature walks.
Can I rent a vacation home with a pool or hot tub in Monterey?
In Monterey, there are several vacation homes available for rent that feature pools and hot tubs, providing travelers with a refreshing and relaxing experience. The area is known for its stunning coastal views and proximity to attractions like the Monterey Bay Aquarium and Cannery Row. Many of the vacation rentals come equipped with amenities such as private pools, hot tubs, spacious outdoor patios, and fully equipped kitchens, making them ideal for both relaxation and entertaining.
Can I find long-stay vacation rentals in Monterey?
A long-stay vacation rental in Monterey 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 Monterey?
In Monterey, there are several pet-friendly house rentals available, offering a welcoming environment for travelers with pets. Many of these vacation homes come equipped with amenities such as spacious backyards, fully equipped kitchens, and cozy living areas, making them great for families or groups.

The area near the coastline provides easy access to scenic spots where pets are welcome, including nearby beaches and parks. For instance, the beautiful coastline along 17-Mile Drive offers stunning views and opportunities for leisurely walks with pets. Additionally, local pet-friendly cafes and shops enhance the experience for those traveling with their furry companions.
Are there any remote work vacation rentals in Monterey?
In Monterey, Massachusetts, there are numerous remote work-friendly vacation rentals available, with around 29 properties to choose from. Many of these rentals offer essential amenities for remote work, including free Wi-Fi in both public areas and individual rooms, ensuring a reliable internet connection for your professional needs. Some accommodations also feature dedicated workspaces or desks, providing a comfortable environment for productivity.

The beautiful coastal town of Monterey offers not only a suitable setting for work but also a charming atmosphere for leisure. Guests can enjoy the nearby scenic coastline and explore local attractions, such as beaches and parks, providing a great balance between work and relaxation. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Monterey vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Monterey 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 Monterey?
In Monterey, vacation rentals commonly feature amenities that enhance comfort and convenience for travelers. Most properties come equipped with kitchens, allowing guests to prepare their own meals and enjoy dining at their leisure. Many rentals also include decks or patios, providing outdoor spaces to relax and take in the scenic surroundings. A cozy fireplace is often available, adding a warm touch for cooler evenings. Onsite parking is typically offered, making it easy for visitors to explore the area with their vehicles. Additionally, porches or lanais are common, offering a charming spot to unwind and soak up the coastal atmosphere.
When is the best time to visit Monterey for a vacation rental?
The best time to visit Monterey for a vacation rental is during the peak season from June to August, with July being particularly popular. This vibrant period attracts travelers looking to soak up the sun along the beautiful coastline and enjoy a variety of outdoor activities. Visitors can partake in whale watching, explore the stunning beaches, or stroll through the renowned Cannery Row, where the lively option enhances the experience.

During these summer months, temperatures typically range from the mid-50s to mid-70s Fahrenheit, providing a comfortable climate ideal for sightseeing and outdoor adventures. Families and friends can enjoy picnics in the picturesque parks or venture out on bike rides along scenic coastal paths.

If you're seeking a more budget-friendly option, consider planning your visit in December. It's cooler, the winter months bring a tranquil charm to Monterey, allowing for peaceful walks along the waterfront and opportunities to witness a different side of the city's beauty.

Ultimately, your choice of when to visit Monterey will depend on whether you prefer the lively summer scene filled with activities or the serene winter ambiance great for relaxation and reflection.
How early should I book a Monterey vacation rental?
Book your Monterey 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 Monterey, Massachusetts, United States of America?
In Monterey, Massachusetts, visitors can enjoy a serene experience surrounded by natural beauty. The nearby Monterey State Forest offers a variety of hiking trails, superb for those who appreciate outdoor activities and scenic views. The charming town center features quaint shops and local eateries, providing a taste of the community's flavor.

For those interested in water activities, the picturesque Lake Garfield is a great spot for swimming, kayaking, and picnicking, with beautiful views of the surrounding landscape. Nearby, the Otis Reservoir provides additional opportunities for boating and fishing, attracting those who love the water.
Can I change or cancel my Monterey home rental booking on Vrbo?
To find Monterey 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 Monterey 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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