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Monterey holiday homes

We found 553 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:18 Dec - 25 Dec

Exterior
Terrace/patio
Interior
Interior
Exceptional
(102 reviews)

Waterfront Cottage 10 Min From Great Barrington

New Marlborough

8% off
NZ$4,194
for 7 nights, 1 cottage
NZ$599 per night
includes taxes & fees
Waterfront Cottage 10 Min From Great Barrington
Kitchen open to living room
Kitchen
2nd  bedroom
Patio off kitchen
Exceptional
(78 reviews)

Charming Cottage, New Marlborough Village Green in the Berkshires

New Marlborough

8% off
NZ$2,799
for 7 nights, 1 cottage
NZ$400 per night
includes taxes & fees
Charming Cottage, New Marlborough Village Green in the Berkshires
Open kitchen to great room, wonderful for cooking and entertaining
The great room with wonderful water views and working fireplace
Sunroom has Queen pull out sofa bed
Hot tub overlooking the lake
Exceptional
(86 reviews)

Spectacular setting on your own private lake close to it all!

Lee

8% off
NZ$7,994
for 7 nights, 1 home
NZ$1,142 per night
includes taxes & fees
Spectacular setting on your own private lake close to it all!
Property grounds
Private kitchen
Terrace/patio
Exterior
Exceptional
(10 reviews)

Beautiful House in the Woods: Huge Yard, Hot Tub

Great Barrington

8% off
NZ$9,837
for 7 nights, 1 home
NZ$1,405 per night
includes taxes & fees
Beautiful House in the Woods: Huge Yard, Hot Tub
Terrace/patio
House facing lake with deck above, canoe and kayak stored on ground level.
Stairway to landing with one LR couch, barstools, kitchen in background
Property grounds
Exceptional
(169 reviews)

4Br/3bath Lakefront/Ski House in Berkshires. Hi speed wifi

East Otis

16% off
NZ$3,653
for 7 nights, 1 home
NZ$522 per night
includes taxes & fees
4Br/3bath Lakefront/Ski House in Berkshires. Hi speed wifi
Living area
Brand new hot tub with privacy gazebo. Imagine soaking in this lovely hot tub, where all  cares can bubble away.
private entrance
 hot tub and bistro table
Exceptional
(76 reviews)

A fun country escape for two! featuring a fireplaces,hot tub, and ping pong

Sandisfield

7% off
NZ$3,046
for 7 nights, 1 room
NZ$435 per night
includes taxes & fees
A fun country escape for two! featuring a fireplaces,hot tub, and ping pong
Staircase
You will love dining and working in this rich and colorful room
The living room flows into the dining room.
A mudroom off the back leads to the large wooden deck
Exceptional
(43 reviews)

An In-Town Beauty with Late Checkout

Great Barrington

8% off
NZ$6,792
for 7 nights, 1 home
NZ$970 per night
includes taxes & fees
An In-Town Beauty with Late Checkout
Living area
Private kitchen
Living area
Exterior
Exceptional
(9 reviews)

Luxurious Mountain Retreat - Private 40-Acre Family Haven

Sheffield

8% off
NZ$11,786
for 7 nights, 1 home
NZ$1,684 per night
includes taxes & fees
Luxurious Mountain Retreat - Private 40-Acre Family Haven
Come and unwind.
Porch opens up from dining room. Ceiling fan and lights above.
Entrance view.
View of the river.
Exceptional
(43 reviews)

Converted Berkshire schoolhouse on a quiet river

New Marlborough

8% off
NZ$3,479
for 7 nights, 1 home
NZ$497 per night
includes taxes & fees
Converted Berkshire schoolhouse on a quiet river
Open and bright main floor living space with stunning views of Laurel Lake.
Open kitchen area with bar seating, great for socializing while you meal prep.
Open kitchen w/ bar & high top seating- sliding door access to second story deck
Second story deck with lake views, dining table for 8, sitting area and grill
Exceptional
(31 reviews)

Lake View Berkshires Retreat - Private & Minutes to Lenox

Lee

16% off
NZ$6,734
for 7 nights, 1 home
NZ$962 per night
includes taxes & fees
Lake View Berkshires Retreat - Private & Minutes to Lenox
Private kitchen
Exterior
Private kitchen
Room
Exceptional
(5 reviews)

Luxury on the River near Tanglewood w/220 EV Charge

Sandisfield

8% off
NZ$3,510
for 7 nights, 1 home
NZ$501 per night
includes taxes & fees
Luxury on the River near Tanglewood w/220 EV Charge
Dining
Outdoor dining
Private kitchen
Room
Exceptional
(11 reviews)

Berkshires Getaway Walk to Distillery - No Pet Fee!

Sheffield

8% off
NZ$5,045
for 7 nights, 1 home
NZ$721 per night
includes taxes & fees
Berkshires Getaway Walk to Distillery - No Pet Fee!
Dining room with butcher block table
Terrace/patio
Queen bedroom
Screened in porch
Exceptional
(103 reviews)

Vacation in a Berkshire Farmhouse

West Stockbridge

9% off
NZ$4,942
for 7 nights, 1 home
NZ$706 per night
includes taxes & fees
Vacation in a Berkshire Farmhouse
Property grounds
Interior
Interior
Kitchen
Excellent
(14 reviews)

Canary Lodge - Berkshires Mountain Retreat - 6 Guests

West Stockbridge

8% off
NZ$6,692
for 7 nights, 1 home
NZ$956 per night
includes taxes & fees
Canary Lodge - Berkshires Mountain Retreat - 6 Guests
Blue House side entry from driveway
River view from window
Great room river view
dining area
Exceptional
(44 reviews)

Renovated Colonial on the River! Fantastic Views

Stockbridge

8% off
NZ$4,792
for 7 nights, 1 home
NZ$685 per night
includes taxes & fees
Renovated Colonial on the River! Fantastic Views
Enjoy a beautiful crisp night under the lights
After a hard day on the trails or a long day on the town, relax in this oasis
Truly nestled on 5+ acres and LESS than 0.8miles to downtown Great Barrington
Seamless entertaining with the wide open concept, living room -kitchen- patio
Exceptional
(29 reviews)

Adventure Ready Ranch Sleeps 10 & 0.7 mi to GB Main St. Wi-Fi + HOT TUB.

Great Barrington

6% off
NZ$7,988
for 7 nights, 1 home
NZ$1,141 per night
includes taxes & fees
Adventure Ready Ranch Sleeps 10 & 0.7 mi to GB Main St. Wi-Fi + HOT TUB.
Interior
Living area
Living area
Lobby
Excellent
(9 reviews)

The Race Mountain House

Sheffield

35% off
NZ$6,672
for 7 nights, 1 home
NZ$953 per night
includes taxes & fees
The Race Mountain House
Room
Interior
Living area
Private kitchen
Exceptional
(61 reviews)

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

Great Barrington

12% off
NZ$2,028
for 7 nights, 1 apartment
NZ$290 per night
includes taxes & fees
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Property grounds
Property grounds
After a day in the snow
We highly recommend the Sauna
Exceptional
(14 reviews)

Secluded Mountainside House with Outdoor Sauna, Surrounded by Trees.

Sheffield

12% off
NZ$4,279
for 7 nights, 1 home
NZ$611 per night
includes taxes & fees
Secluded Mountainside House with Outdoor Sauna, Surrounded by Trees.
Private kitchen
Outdoor dining
Private kitchen
Living area
Exceptional
(13 reviews)

Charming Berkshire Farmhouse: Your Cozy Retreat Awaits!

Monterey

8% off
NZ$4,878
for 7 nights, 1 home
NZ$697 per night
includes taxes & fees
Charming Berkshire Farmhouse: Your Cozy Retreat Awaits!
Dining Area, view into living room. Games, books, records all available for your enjoyment!
Ultimate Relaxation!  The hot tub will be warm and waiting for your arrival
Welcome Home!
Private kitchen
Exceptional
(9 reviews)

Best of the Berkshires + Hot Tub by Evergreen Home

Great Barrington

11% off
NZ$5,849
for 7 nights, 1 home
NZ$836 per night
includes taxes & fees
Best of the Berkshires + Hot Tub by Evergreen Home
Interior
Front Entrance
Interior
dining room
Exceptional
(15 reviews)

Beautiful Berkshire Home - Enjoy summer, fall & winter attractions

Sheffield

8% off
NZ$7,444
for 7 nights, 1 home
NZ$1,063 per night
includes taxes & fees
Beautiful Berkshire Home - Enjoy summer, fall & winter attractions
Interior
Property grounds
Exterior
Room
Wonderful
(6 reviews)

The Serendipity Spot

Great Barrington

7% off
NZ$2,368
for 7 nights, 1 apartment
NZ$338 per night
includes taxes & fees
The Serendipity Spot
Room
Private entry is with the parking in the rear of the house.
Our hanging egg chair is the most popular seat in the house #Instagram yourself!
Exterior
Exceptional
(24 reviews)

New Reno, New Everything! Crisp and Clean 2 Bedroom in Stockbridge Center.

Stockbridge

24% off
NZ$3,205
for 7 nights, 1 apartment
NZ$458 per night
includes taxes & fees
New Reno, New Everything! Crisp and Clean 2 Bedroom in Stockbridge Center.
  • 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, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

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)
  • Bousquet Ski Area (16.7 mi / 26.8 km)
  • Umpachene Falls Park (6.6 mi / 10.7 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)
  • Lake Mansfield Park (8.1 mi / 13.1 km)
  • Otis Reservoir (9 mi / 14.4 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.
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.
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 Bookabach.
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.
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.
Are all fees included in the Monterey holiday homes prices shown on Bookabach?
Bookabach 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.
Are there any Monterey holiday homes with parking?
Bookabach offers a wide selection of holiday homes 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 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.
Are there any discounts for Monterey holiday homes?
You can find great discounts on holiday homes in Monterey on Bookabach, 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.
Can I change or cancel my Monterey holiday home booking on Bookabach?
To find Monterey holiday rentals with free cancellation, just use Bookabach'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". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Monterey?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach'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 favourites, and build the perfect itinerary together.
How early should I book a Monterey holiday home?
Book your Monterey holiday home 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 Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Monterey?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Monterey to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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.
Why should I join Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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