Photo by Elizabeth Massa Peroulakis

Monterey holiday lettings

We found 528 holiday rentals — enter your dates for availability

Discover a selection of 25 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:24 Oct - 31 Oct
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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)
  • Kennedy Park (14.3 mi / 22.9 km)
  • Bousquet Ski Area (16.7 mi / 26.8 km)
  • Otis Ridge (5.8 mi / 9.3 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 most popular type of holiday rental accommodation in Monterey?
Houses are the most popular kind of holiday rental in Monterey, according to our data. Even if you've got something bigger or smaller in mind, Vrbo has holiday homes in loads of sizes and shapes. Look through our options to find your ideal match.
How much does it cost to rent a holiday rental in Monterey?
The average price for a holiday home in Monterey is determined by a number of factors, including season, length of stay and property type. Whether you're searching for a sprawling villa with room to move around or a quaint cabin ideal for just you and the kids, just add your dates of travel to find stays with fantastic value.
How much does it cost to rent a beach house in Monterey?
Prices for beach houses in Monterey may vary depending on the style and size of the property and when you're travelling. All you have to do is enter your travel dates into Vrbo and how many guests to view available options and prices. From there you can use our filter tool to refine your search results by ratings, nearby activities and more.
Are there pet-friendly holiday rentals in Monterey?
With 26 properties that welcome four-legged guests, your furry friend can also come along on your Monterey holiday. Use the filter tool to search our pet-friendly holiday rentals and find a stay that'll set tails wagging on Vrbo.
Can I rent a house with a pool in Monterey?
Mark the "pool" box in our filter tool and you'll find two houses with private pools in Monterey on Vrbo. Morning soak, afternoon splash or midnight swim? Downtime is up to you when your holiday home boasts its own swimming pool.
What are popular rental amenities in Monterey?
The most popular rental amenities people look for in Monterey are a fireplace, a firepit and tennis. Whether you're going on holiday with friends, family or even pets, Vrbo holiday properties include the best amenities for hanging out with the people that matter most.
Are there large group holiday rentals in Monterey?
Monterey has six holiday homes that can fit 10 or more guests. These stays come with plenty of space to enjoy good times with your favourite people.
Are there holiday rentals in Monterey that welcome kids?
Monterey has 26 family-friendly holiday rentals to choose from. And booking a stay that welcomes little ones is easy with our "Properties good for families" filter. Besides having the whole place to yourselves, you'll also get access to conveniences and perks like living rooms, full kitchens and private pools.
What are the top attractions for families in Monterey?
You'll find loads of wonderful things to see and do with the family in Monterey, such as:

  • Umpachene Falls Park
  • County Beach
  • Housatonic River Walk

Are there one-bedroom holiday rentals in Monterey?
Yes, Monterey has two one-bedroom rentals available. Usually situated in desirable areas because of their smaller size, a one-bedroom property is great if you're getting away with a friend or your partner. And with home comforts like wireless internet and more privacy than a standard hotel, you'll be able to kick back and relax while exploring this terrific destination.
Can I find two-bedroom holiday rentals in Monterey?
Gather your loved ones and experience complete comfort and privacy in one of the five two-bedroom holiday properties Monterey has to offer.
Are there holiday rentals with WiFi in Monterey?
Whether you'd like to stay in touch with the news, reply to emails or surf social media, there are 11 holiday homes with WiFi in Monterey. Check the "WiFi" box when searching on Vrbo and stay connected on your holiday.
How can I find holiday rentals with air conditioning in Monterey?
Monterey has 20 holiday rentals where you can chill out in air-conditioned comfort. To find a stay on Vrbo with this perk, enter your dates of travel and use the convenient filters to select the "air conditioning" box.
How old do you have to be to rent a holiday rental in Monterey?
The minimum required age is generally 16, 18 or 21. It can differ between properties on Vrbo, so look at the rules of your preferred Monterey stay before booking.
How long can I rent a holiday rental in Monterey for?
The length of time you can rent a holiday rental in Monterey is up to the property. Simply enter your preferred dates to see a list of options offering extended stays. With loads of creature comforts such as washing machines and air conditioning, as well as some offering discounted weekly or monthly prices, you're sure to find somewhere just right to call your home away from home in Monterey.

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