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Monterey holiday lettings

We found 531 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.

Holiday rentals with weekly discounts - Monterey

Showing deals for:13 Feb - 20 Feb

Image gallery for Little House in the Woods by Evergreen Home

Welcome to the Little House!
10 out of 10, Exceptional, (34 reviews)
Exceptional
(34 reviews)

Little House in the Woods by Evergreen Home

Sheffield, MA

11% off
Price is £2,142
for 7 nights, 1 home
£306 per night
includes taxes & fees
Little House in the Woods by Evergreen Home

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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)
  • 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)
  • Les Trois Emme Winery (3.8 mi / 6.2 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:

  • Ashintully Gardens (3.2 mi / 5.2 km)
  • 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)

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 planning a holiday rental in Monterey, Massachusetts, one of the best areas to consider is the vicinity around Lake Garfield. This picturesque location offers a tranquil atmosphere, great for those looking to unwind amidst nature. The lake itself is a popular attraction, providing opportunities for swimming, kayaking, and fishing, making it an ideal spot for water enthusiasts. Nearby, you can also explore the scenic trails of the Monterey State Forest, which is great for hiking and enjoying the stunning landscapes.

Another charming area is the town centre, where you can experience the local culture and community. Although smaller in size, the town centre offers a selection of delightful properties that capture the essence of New England charm. Visitors can easily access attractions such as the beautiful Monterey Public Library, which often hosts community events and showcases local history.
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, Massachusetts, travellers should consider the picturesque area along the coastline, particularly near the scenic vistas of the Atlantic Ocean. The neighbourhood around the local beaches, such as those near the historic waterfront, presents a variety of rental options that offer stunning ocean views and immediate access to sandy shores. Many properties in this area feature amenities such as spacious outdoor decks, private gardens, and fully equipped kitchens, ideal for families or groups looking to enjoy leisurely beach days.

Additionally, the surroundings of the local parks, such as the nearby state parks, provide opportunities for hiking and picnicking, enhancing the overall experience. Many beach houses in this vicinity come with outdoor showers, which are great for rinsing off after a day at the beach, as well as barbecue facilities for enjoying evening cookouts. The charming village atmosphere also means that visitors will find local shops and restaurants within easy reach, adding convenience for those looking to explore the culinary offerings of the region.
Where are the best Monterey ski resort rentals?
For skiing near Monterey, Massachusetts, the best options for rentals can be found in the nearby Berkshires, particularly in towns like Lenox and Great Barrington. These areas offer convenient access to popular ski resorts such as Bousquet Ski Area and Catamount Ski Area, both of which feature a variety of runs suitable for different skill levels.

In Lenox, visitors can expect to find charming cottages and lodges, often equipped with amenities such as fireplaces, spacious living areas, and kitchens for preparing meals after a day on the slopes. Many properties also include outdoor spaces where guests can unwind and enjoy the scenic winter landscape.

Great Barrington, known for its vibrant arts scene and local dining options, provides additional rental choices, including stylish apartments and family-sized homes. Many of these accommodations come with modern conveniences like Wi-Fi, hot tubs, and access to local amenities, making them ideal for both relaxation and adventure.
What is the most popular type of holiday rental accomodation in Monterey?
In Monterey, holiday houses are the most popular type of accommodation, with around 23 available in the area. These properties are typically spacious and often feature multiple bedrooms, fully equipped kitchens, and inviting living areas, making them ideal for families or groups looking to enjoy the beautiful surroundings. Additionally, there are several charming cottages, chalets, and cabins that provide a more rustic experience, often located in scenic locations. Many of these rentals come with outdoor spaces, such as gardens or decks, allowing guests to soak in the fresh air and stunning views of the nearby landscape.
Are there any family house rentals in Monterey?
In Monterey, Massachusetts, there are numerous family-friendly house rentals available—specifically around 26 options to choose from. This charming coastal town is great for families seeking a memorable getaway, with properties located in neighbourhoods such as the historic district and along the scenic waterfront.

Many of these homes feature spacious living areas, fully equipped kitchens ideal for preparing family meals, and outdoor spaces for children to play and relax. Visitors can expect amenities like Wi-Fi, laundry facilities, and comfortable furnishings that make for a welcoming environment after a day of exploring.
Can I rent a holiday home with a pool or hot tub in Monterey?
In Monterey, Massachusetts, there are several holiday homes available for rent that feature pools or hot tubs, making it an attractive option for travellers seeking relaxation and leisure. The area is known for its picturesque coastal scenery and charming small-town atmosphere, providing a great backdrop for a holiday retreat.

Many of these properties come equipped with amenities such as private swimming pools, outdoor hot tubs, and spacious patios for enjoying the beautiful surroundings. Inside, travellers can expect fully equipped kitchens, comfortable living areas, and often multiple bedrooms to accommodate families or groups.
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, Massachusetts, there are several pet-friendly house rentals available for those travelling with their furry companions. The area offers a charming coastal atmosphere, with many properties featuring amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, ensuring a delightful stay for both pets and their owners.
Are there any remote work holiday rentals in Monterey?
In Monterey, Massachusetts, there are numerous remote work holiday rentals available, with around 34 options to choose from. This picturesque coastal town offers a tranquil environment great for those looking to blend work and leisure. Many of the properties are well-equipped with essential amenities such as high-speed Wi-Fi, dedicated workspace including desks and ergonomic chairs, and laptop-friendly setups, ensuring a comfortable working atmosphere. 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 rentals typically feature essential amenities that cater to the needs of travellers. Most rooms come equipped with a kitchen, allowing guests to prepare their own meals, along with a refrigerator and stovetop for convenience. Additionally, many rentals include a dishwasher, which adds to the ease of maintaining a clean and tidy space during a stay.
When is the best time to visit Monterey for a holiday rental?
The most popular time to visit Monterey for a holiday rental is during the peak summer season from June to August. This vibrant period attracts travellers, drawn to Monterey's stunning coastal scenery, beautiful beaches, and a number of outdoor activities. The mild climate, with temperatures averaging in the low to mid-20s Celsius, makes it ideal for exploring the local attractions like the world-famous Monterey Bay Aquarium or enjoying water sports along the coastline.

July is particularly bustling, as it's when many holidaymakers flock to the area to soak up the sun and participate in various local festivals and events. The atmosphere is lively, with plenty of opportunities for sightseeing, beach activities, and enjoying fresh seafood at local eateries.

For those looking to enjoy Monterey at a more relaxed pace and at a better value, consider visiting in December. It's cooler, with temperatures around 5 to 10 degrees Celsius, the winter months offer a unique charm. You can experience the beauty of the coastline without the crowds, and the festive holiday decorations add a delightful touch to the town.
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 variety of attractions located within the beautiful natural landscape. The nearby Monterey State Forest offers opportunities for hiking and exploration, where you can immerse yourself in the region's serene woodlands and wildlife. The tranquil shores of Lake Garfield provide a picturesque setting for swimming, kayaking, and picnicking, making it a popular spot for both relaxation and recreation.
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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
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.

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