Photo by Fun Travelog

Monterey holiday lettings

We found 560 holiday rentals — enter your dates for availability

Discover a selection of 24 homes and other holiday rentals in Monterey that are perfect for your trip. Holiday homes provide the amenities that you need and want for your family, friends or furry companion, such as air conditioning and cable TV. At the end of the day, you'll be able to choose a property to rent that has what everyone needs, including accessible or non-smoking choices.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Why visit Monterey

  • Stunning Scenery: Monterey offers breathtaking landscapes perfect for outdoor enthusiasts and romantic getaways.
  • Cultural Experiences: Explore historic houses and local shrines for a glimpse into the town's rich heritage.
  • Monterey Museum: A must-visit attraction showcasing local art and history, enhancing your cultural exploration.
  • Variety of Accommodations: Choose from charming holiday homes, stylish condos, or delightful cottages for a comfortable stay.
  • Family-Friendly Atmosphere: The welcoming environment makes Monterey an ideal destination for families and couples alike.

Popular types of accommodation in Monterey

Planning a getaway to the picturesque town of Monterey? The excitement begins with selecting your ideal accommodation. Explore a variety of options, including charming private holiday homes, stylish condos, and delightful cottages. Whether you're searching for Monterey holiday rentals, lettings, or apartments, you'll find the perfect base for your adventures. Enjoy transparency, savings, and reassurance as you embark on your memorable trip to this stunning destination.

  • Houses: These are the top choice for visitors seeking spacious and comfortable accommodations, ideal for families or groups.
  • Condos: A popular option, condos offer modern amenities and often come with stunning views, perfect for couples or small families.
  • Cottages: Quaint and charming, cottages provide a cozy retreat, often situated near nature or the lakeside.
  • Apartments: Convenient and versatile, apartments are great for those wanting a home-like experience in Monterey.
  • Cabins: Rustic and inviting, cabins offer a unique getaway experience, surrounded by the beauty of nature.**

Top attractions near Monterey

Monterey, Massachusetts, is perfect for outdoor and romantic getaways, boasting stunning scenery and a variety of attractions. Explore historic houses, serene lakes, and local shrines, all catering to those seeking adventure and cultural experiences. Don't miss the Monterey Museum and other attractions for a delightful coastal escape that promises both relaxation and exploration.

  • National Shrine of the Divine Mercy: A serene sanctuary located 5.6km from Monterey, this shrine offers a peaceful atmosphere for reflection and spiritual enrichment, surrounded by beautiful gardens and a sense of community.
  • Lake Buel: Situated 1.9km away, Lake Buel is perfect for outdoor enthusiasts, featuring a picturesque beach, stunning scenery, and a romantic setting ideal for picnics and leisurely strolls.
  • Norman Rockwell Museum: Located 6.2km from Monterey, this art museum showcases the iconic works of Norman Rockwell, immersing visitors in American culture and storytelling through art.

Things to do recommended for couples

For a romantic getaway in Monterey, indulge in skiing at Ski Butternut, just 3.7km away. Enjoy a cultural evening at Jacob's Pillow, 5.0km from town, or savour fine wines at Les Trois Emme Winery, a mere 2.5km away, perfect for couples seeking romance and entertainment.

Things to do recommended for families

Your family will love exploring the tranquil Goose Pond Reservation, just 4.3km from Monterey, perfect for relaxation. Lake Mansfield Park, 5.0km away, offers a serene setting, while the scenic Tyringham Cobble, located 3.1km from Monterey, invites you to unwind amidst nature.

Things to do recommended for groups

Groups visiting Monterey can enjoy a shopping spree at the Lee Premium Outlets, embark on an adventurous hike along the Housatonic River Walk, and experience a captivating performance at the Mahaiwe Performing Arts Center, all within 5.0km of the town.

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

If you're travelling with a group, family, pets, or seeking longer stays, it's essential to prioritise your preferences when filtering options. Here are some helpful Vrbo booking tips for you.

  • Traveling to Monterey with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and many more on Vrbo.
  • Traveling to Monterey with young kids: Traveling with young children can be quite demanding. It's important to prioritise their comfort and safety, along with ensuring that suitable amenities are available, like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Monterey: For many families, a holiday wouldn’t feel complete without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Monterey: If you're in search of holiday rentals that offer discounts for month-long stays, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to include amenities like a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay near Monterey

Monterey, Massachusetts, is a delightful holiday destination perfect for outdoor enthusiasts and couples seeking a romantic getaway. Surrounded by stunning scenery, visitors can explore the charming local atmosphere, which is both family-friendly and inviting. Nearby attractions in Monterey County offer a blend of relaxing beach experiences and picturesque landscapes, making it an ideal location for a memorable escape. From tranquil walks to scenic views, Monterey promises a rejuvenating experience for all travellers.

  • Lenox: Located 8.1km from Monterey, Lenox is a charming town renowned for its vibrant arts scene and romantic ambiance. Visitors flock to Lenox for entertainment-themed experiences, with highlights including music concerts and theatrical performances. The town also provides family-friendly activities, particularly in its beautiful natural settings. Nearby, you'll find picturesque lakes and mountains, perfect for a leisurely stroll or a picnic. The local event conference venues frequently host cultural events, making it a lively spot for visitors seeking a blend of relaxation and entertainment.
  • The Berkshires: A mere 1.9km from Monterey, The Berkshires is a breathtaking region celebrated for its outdoor adventures and stunning scenery. This area attracts nature enthusiasts keen on skiing at the various ski fields and resorts. The Berkshires is not only a haven for winter sports but also offers year-round activities, including hiking and exploration of its lush landscapes. With its tranquil lakes and majestic mountains, it’s an ideal destination for those looking to immerse themselves in nature while enjoying a range of recreational pursuits.
  • Great Barrington: Situated 5.0km from Monterey, Great Barrington is a vibrant city known for its adventurous spirit and sports activities. Skiing enthusiasts will appreciate the local ski fields and resorts, making it an excellent choice for winter sports. The town also boasts beautiful lakes and scenic mountain views, providing a perfect backdrop for outdoor activities. Additionally, Great Barrington is close to national state parks, which offer ample opportunities for hiking and exploring the great outdoors, ensuring a memorable experience for all who visit.

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 a breeze

Are you hoping to save on your upcoming holiday? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you might find considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, simply use our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan new journeys, pick up right where you paused, or manage your travel arrangements with ease. You can now conveniently access the properties you've saved and booked under Potential, Upcoming, or Current Trips. To explore the Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Why people love visiting scenic 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 trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in Monterey

Do you want to find top things to see and do while you're in the area? Venture out of your cosy holiday rental and experience everything that Monterey has to offer. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • 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)
  • Kennedy Park (14.3 mi / 22.9 km)
  • Bousquet Ski Area (16.7 mi / 26.8 km)

Exploring the natural landscape of Monterey

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

  • Lake Buel (3.3 mi / 5.4 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)
  • Pyramid Lake (7.8 mi / 12.6 km)
  • Lake Mansfield Park (8.1 mi / 13.1 km)

Transport to and around Monterey

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 17.5 mi (28.1 km) from the city centre. 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 when booking a holiday rental?
When considering a holiday rental in Monterey, Massachusetts, the area around Lake Garfield is an excellent choice. This picturesque neighbourhood offers a serene lakeside setting, making it ideal for those looking to unwind in nature. Visitors can enjoy activities such as swimming, kayaking, or simply relaxing by the water's edge.

Additionally, the nearby Beartown State Forest is a fantastic attraction, featuring miles of hiking trails that wind through beautiful woodlands. For a touch of local culture, the quaint town centre provides charming shops and eateries, superb for a leisurely afternoon stroll.

While the exact number of properties may vary, the availability in this area is generally good, providing a range of options from cosy cabins to spacious homes.
How much does it cost to rent a holiday home in Monterey?
Prices for holiday 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 holiday 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, the Cannery Row area is an excellent choice, renowned for its picturesque coastal views and vibrant setting. Many properties here offer amenities such as outdoor decks with stunning ocean vistas, fully equipped kitchens, and easy access to local attractions. Visitors can enjoy nearby attractions like the Monterey Bay Aquarium and various shops and restaurants, making it a convenient spot for families and groups.

Further along the coast, the area around Asilomar State Beach provides a more tranquil setting, with charming beach houses located among the dunes. These rentals often feature amenities such as private patios, fire pits, and direct beach access, superb for those looking to unwind by the ocean. The nearby Pacific Grove also offers delightful options, with properties that boast lovely gardens and proximity to scenic walking trails along the coastline.

For those seeking a blend of adventure and relaxation, the 17-Mile Drive offers stunning views and access to iconic landmarks like the Lone Cypress. Rental properties in this area often come with upscale amenities, including hot tubs and spacious living areas, providing a luxurious beachside experience.
Where are the best Monterey ski resort rentals?
For skiing in Monterey, Massachusetts, the nearest ski area is the nearby Berkshire East Mountain Resort, which offers a variety of slopes suitable for all skill levels. For rentals, consider looking in the surrounding towns of Charlemont and Hawley. In Charlemont, you'll find charming cabins and lodges that often come with amenities such as fireplaces, fully equipped kitchens, and outdoor decks that allow for relaxation after a day on the slopes.

Many properties in this area cater to families and groups, providing ample space for gathering and unwinding. Some rentals may include features like game rooms or hot tubs, enhancing the après-ski experience. In addition, the town of Hawley offers more secluded options, with rustic cottages set amidst beautiful natural surroundings, superb for those looking to escape into nature.

The region is also known for its stunning views and outdoor activities beyond skiing, with hiking trails and scenic spots nearby, allowing guests to enjoy the beauty of the Berkshires throughout the year.
What is the most popular type of holiday rental accomodation in Monterey?
In Monterey, holiday houses are the most popular type of holiday rental, with around 76 available throughout the area. These houses are typically spacious, offering multiple bedrooms and fully equipped kitchens, making them ideal for families or larger groups. Many also feature outdoor spaces like patios or gardens, superb for enjoying the coastal climate after a day exploring the nearby attractions, such as the stunning coastline and local parks.

Cottages are also a top option, with about 28 available. These provide a charming, quaint experience, often set in picturesque surroundings. They usually come with cozy living areas and kitchens and are superb for couples or small families looking for a more intimate setting. Additionally, there are several cabins and chalets available, offering a rustic escape for those wanting to immerse themselves in nature while still enjoying modern comforts.
Are there any family house rentals in Monterey?
In Monterey, Massachusetts, there are some family-friendly holiday rentals available, offering a variety of options for those travelling with children. The area features spacious homes with amenities like fully equipped kitchens, comfortable living rooms for family gatherings, and outdoor spaces where kids can play or enjoy a picnic.

Visitors can explore the beautiful coastline, with nearby attractions including the scenic beaches and walking trails that are great for family outings. The locale also boasts access to charming local shops and restaurants, ensuring a delightful experience for all ages.
Can I rent a holiday home with a pool or hot tub in Monterey?
In Monterey, there are several holiday homes available for rent that feature either pools or hot tubs, making it an appealing destination for those seeking relaxation. The area boasts picturesque coastal views and a rich marine environment, with properties often located near the ocean or in serene residential neighbourhoods.

Travellers can expect a variety of amenities in these rentals, including private pools, hot tubs, outdoor seating areas, and well-equipped kitchens, great for preparing meals after a day of exploring the nearby attractions.
Can I find long-stay holiday rentals in Monterey?
A long-stay holiday rental in Monterey 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 Monterey?
In Monterey, there are several pet-friendly house rentals available, providing a welcoming environment for those travelling with pets. Many of these holiday homes come equipped with amenities such as fully stocked kitchens, spacious living areas, and outdoor spaces where pets can roam freely. The charming neighbourhoods of Monterey offer a mix of coastal beauty and convenience, with some properties featuring stunning views of the ocean or easy access to local beaches.

Additionally, the area is near pet-friendly points of interest like the scenic coastal trails of the Monterey Bay Coastal Recreation Trail, where both visitors and their furry companions can enjoy leisurely walks along the stunning coastline. Nearby parks, such as the lovely Dennis the Menace Park, provide ample space for pets to play and interact.
Are there any remote work holiday rentals in Monterey?
In Monterey, Massachusetts, there is a good selection of remote work holiday rentals available, with around 116 options to choose from. The town, known for its picturesque coastal scenery and serene atmosphere, is an excellent choice for those looking to blend work with leisure. Many of these properties come equipped with essential amenities for remote work, including Wi-Fi, dedicated workspaces, and comfortable living areas that make it easy to focus while enjoying the stunning surroundings.

Travellers can expect a variety of accommodations, from cozy cottages to spacious homes, often featuring modern conveniences such as fully equipped kitchens, outdoor spaces for relaxation, and easy access to local attractions. The area is close to natural points of interest, including beautiful beaches and scenic trails, allowing for refreshing breaks during the workday. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Monterey holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Monterey 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 Monterey?
In Monterey, popular holiday rental amenities typically include kitchens, allowing guests to prepare their own meals during their stay. Many properties also feature decks or patios, providing outdoor spaces to relax and enjoy the fresh air. Fireplaces are common as well, offering a cosy atmosphere, especially during cooler evenings. Onsite parking is often available, making it convenient for those travelling by car. Additionally, some rentals come with porches or lanais, great for enjoying the surrounding beauty.
When is the best time to visit Monterey for a holiday rental?
July is the most popular time to visit Monterey, drawing in holidaymakers eager to experience the vibrant summer atmosphere. The peak season spans from June to August, during which visitors can enjoy the stunning coastal views, delightful weather, and a variety of outdoor activities. With average temperatures ranging from 15 to 20 degrees Celsius, this period is superb for exploring the scenic beaches, hiking the nearby trails, or simply relaxing by the ocean.

If you're looking for a more tranquil experience, consider planning your trip in December. Although this month is part of the low season, it offers a unique charm with fewer tourists, allowing you to enjoy the serene beauty of Monterey at a more leisurely pace. You can take peaceful walks along the coastline and appreciate the crisp winter air, all while soaking up the area's natural beauty.

Ultimately, the best time to book a holiday rental in Monterey depends on your preferences.
How early should I book a Monterey holiday rental?
Book your Monterey 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.
What are the top attractions in Monterey?
In Monterey, Massachusetts, visitors can enjoy a tranquil and picturesque setting with several attractions worth exploring. The nearby Mount Greylock State Reservation offers stunning views and hiking opportunities, with trails for various skill levels. This area is great for outdoor enthusiasts looking to connect with nature.

The charming village of Monterey itself features beautiful landscapes and historic architecture, making it a lovely spot for leisurely strolls. Additionally, the nearby Beartown State Forest provides ample opportunities for hiking, picnicking, and enjoying the serene environment.

Those interested in art and culture may appreciate the proximity to cultural attractions in the surrounding areas, including galleries and museums that showcase local talent.
Can I change or cancel my Monterey home rental booking on Vrbo?
To find Monterey 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 Monterey 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.

More holiday ideas