Monterey is a small quaint town in the state of Massachusetts and a popular destination for a quiet short getaway. The town is located at a two-hour drive from Boston, and a two-and-a-half-hour drive from New York City in its neighbouring state. The small town is most well-known for being close to the Beartown State Forest, which is great for those who love hiking and the beautiful scenic views of the forest and lake. The Bidwell House Museum, a local historic art house, and museum, is also a common tourist attraction. Further away from the town are also other nature reserves and the like, such as Upper Goose Pond and Lake Buel. Alongside the famous Monterey Dunes rentals, you will also find great lakehouses for a family vacation or a quaint little cosy hideaway for your accommodation needs. Read on to find the best Vrbo vacation rentals in Monterey, Massachusetts!
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on April 08, 2024.
1. Lovely Vrbo rental with gorgeous mountain views (from USD 695)
Located in the county of Southern Berkshire, this Vrbo is only 15 minutes away from the town of Great Barrington.
Guests can wake up to breathtakingly beautiful views of the majestic mountains that can be sighted from the bedroom windows. You can gather with family and friends on the plush couch armed with tubs of popcorn and colas and enjoy movie marathons on cable TV. Children can have a good time indoors with games and puzzles. Free WiFi and car parking facilities are available.
Top guest reviews
Amenities & Room:
beds also super comfortablethe house property is incredible very roomy well-kept and comfortableCleanliness:
clean and the decor of the house was beautifulRead more reviewsHost:
johanna the owner was very proactive and communicativejohanna was an excellent and responsive hostsuch an amazing process from start to finish house was amazing and host was so responsivewonderful property with a very accommodating and responsive hostthe owner is an interior designer so it doesn’t feel like a rental
2. The Hupi House (from USD 283)
This beach house in Monterey is only a four-minute drive from the pristine waterscape of Lake Garfield. It rests atop a hill and is surrounded by lush greenery. You will feel like you are being cradled in the lap of nature when you are here.
Guests who love homemade fare can prepare hearty meals in the well-equipped kitchen and savour them on the patio while enjoying gorgeous views of the looming mountains and the lake. Bonfire evenings can be enjoyed in the warmth of the outdoor fire pit.
Top guest reviews
Amenities & Room:
the house is super cozy and we couldn't of had a better timeCleanliness:
highly recommend cabin/house is very nice clean and speciousit has enough space for several people to stay comfortably and was clean and as advertisedthe house is well stocked with supplies and cooking needs and was very cleanbeds are super comfortable and the house is very cleanRead more reviewsHost:
greg is a very understanding and welcoming host promptly responding to and if possible accommodating requestsowner was very responsive and helpful every time i had a questiongreg was very responsive and helpful the whole weekend
3. A cosy family chalet (from USD 200)
This cosy vacation home rental in Monterey is located right behind the Bidwell House Museum, one of the major tourist attractions of the town. There are two bedrooms upstairs and one bathroom downstairs. You can fit two more people on the couch which pulls out to a queen-sized bed in the living room. There is also an extensive kitchen and dining area, as well as a screened porch to comfortably enjoy the view outdoors. It is just minutes away from town, where you can get groceries and meals.
Top guest reviews
Amenities & Room:
The beds and furniture were comfortableIt is fully stocked for anything you need in the kitchen from baking to meat thermometerThe king-sized best was super comfyThe bedroom was comfortable and there were lots of bed linens towelsOur only complaint was the internet serviceCleanliness:
The house was very suitable for over night guests and dinner partiesThe whole cottage is maintained beautifully and decorated wonderfullyIt's quite lovely and had everything we neededThe house is very clean and not as run-down (that's harsh) as it may appear in the photosHost:
Super child friendly as wellValerie herself was very communicative and obviously cares about her house and her rentersValerie was a great hostnicely decorated all the comforts of home and nice extra gratitutiesWe were thankful for good all-weather tiresRead more reviewsLocation:
We enjoyed every minute of our time at the ChaletWe loved the decorations throughout the houseBeautifully maintained lot of amenitiesThe location was perfect for skiing at the ButternutThe house looks better in person than in the photos--
4. An amazing log cabin (from USD 826)
This amazing log cabin Vrbo in Massachusetts can fit a huge family or group of friends, in three bedrooms as well as a few extra beds in the basement. Just in the backyard of the cabin, you can find a hot tub, fire pit, hammock, outdoor shower, and a beautiful screened-in porch. The kitchen is also fully stocked and there is also a nice living area with a crackling fireplace. It is secluded and quiet for a relaxing getaway, but also close to the beach and town.
Top guest reviews
Amenities & Room:
There was plenty of room and privacy for everyoneThe kitchen is well equipped everything we needed was easy to findThe kitchen is great with a dining table big enough for the whole family and plenty of room to have a few people in their cooking at the same timeThe living room is warm and cozy with a lovely fireplace We enjoyed several rounds of pool in the game room downstairs -The game room is an added bonus with a large couch tv pool table and darts - and extra bedsCleanliness:
It's extremely clean and organized and tastefully decoratedVery clean and well equippedEverything was extremely clean and the kitchen is amazingMy children were gaga over the new and very clean outdoor hot tubHost:
Jim the host was available and helpfulJim was very responsive and checked with us to make sure everything was goodThe home is extremely well cared for and the owner very kind available and clear with all of his instructionsWe all enjoyed billards dartsJim is a great host and makes things clear and easyRead more reviewsLocation:
This cabin was tucked away in the woods but not too far away from Great BarringtonWe ate at the really amazing restaurants in Great BarringtonWe also enjoyed country walks swimming at Lake GarfieldWe enjoyed the quiet peaceful setting as we gazed into the woods and listened to nature's summerit's well stated on their page
5. A marvellous lakeside house (from USD 488)
This huge and spacious home can fit up to twelve people, so it’s perfect for a huge family vacation or a getaway with a group of friends. The lakeside house has four bedrooms and five bathrooms, as well as three common areas. The kitchen is well-equipped with new stainless steel appliances. The house also comes with outdoor seating and a gas grill on the outdoor deck. This beautiful home is also close to the Lake Garfield beach, as well as the Monterey town store for groceries.
Top guest reviews
Amenities & Room:
It had plenty of room for everyone to be comfortableThere was plenty of space and options for our groupThe kitchen is very well equippedThe bedrooms were comfortable and loaded with tons of storage There wereWhile it was not lake weatherCleanliness:
The bedrooms are spacious and extremely comfortable as are the bathroomsAnd it was totally and immaculately cleanThere were fresh towels and Fresh Linen soaps in the bathrooms and games and books for the kids to play withBeautiful clean and spacious houseThe deck was lovely and very convenient for use of the barbecueHost:
extra kid friendly items books chairsShe responded very quickly to questions I had before rentingThe owner was especially personable and helpfulWe all had a really wonderful time Everything was set up and taken careSome of the appliance look brand new and all workedRead more reviewsLocation:
The location was convenient for the surrounding attractionsThe location is private surrounded by woods just a short walk to the beach on Lake Garfieldit is only a few minutes to walk to the beach and kayakingA beautiful clean and safe place to swim CindyUpdated amenities Five minute walk to the lake/beach Close to Lenox and Stockbridge
6. A modern home for four (from USD 349)
This family vacation home is very well equipped, with kayaks, paddle boats, rowboats, and floats to enjoy swimming and paddling by the beautiful Lake Garfield. The four bedrooms can fit up to ten people in this huge home. It is a modern and tastefully decorated home that maintains the rustic feel of the wood. It is centrally located to all that Berkshire has to offer in the area, from shopping and dining the town, to hiking and swimming by the lake.
Top guest reviews
Amenities & Room:
Wonderful deck off of dining room overlooking the lakeI enjoyed coffee and a crossword puzzle on the deck at 6The lake was great Access to water off deck was great and guests enjoyed the kayaking and paddle boatsI finally tried the app WAZE and it took me right to the front doorthe kitchen is fully equipped and we took advantage of the grillHost:
convenient Steven was very helpfulThe owners made themselves available by text or phone to help as needed and were both gracious and accommodating One word of advice-we has some trouble finding the house on a dark and rainy nightWe had two children with us ages 10 and 12 and they loved itSUPs Steven was easy to communicate with and always responsive Nice location near Great Barrington and Leethe phones and other devices were abandoned in favor of a rousing game of hide and seek I loved that time with the kidsRead more reviewsLocation:
and it's many nooks and cranniesWe had a delicious meal at Koi Chinese Restaurant in Great Barrington and saw a play in PittsfieldThe owners' attention to detail and responsiveness rounded out a perfect experienceHouse is charmingly quaint with lots of nooks and crannies on multiple levels well equipped for adults and children alike Lakeside location is very attractive and enjoyable Not much sun penetrat...well furnished interesting design without being fussy Lots of space to spend time with family lots of places to escape to for some "me time"
7. A waterfront country home with private dock (from USD 357)
This beautiful country home is great for those who want to spend time by the lake. Located right by Lake Garfield, the house has a deck that extends to a private dock off the coast of the lake, as well as two paddle boards available for use. Inside, there is a large and spacious living room, as well as a fully equipped kitchen and dining area. There are three bedrooms for up to six people and two bathrooms. Besides being near the lake, the house is also about a mile (1.6km) away from the Monterey Public Library in town.
Top guest reviews
Amenities & Room:
Having three spacious bedrooms 2 new bathrooms and a great kitchen overlooking the woods and the lake-Loved the beautiful view of the lake from the house and easy water access Would definitely book againThe rooms are spacious and so very comfortable and the pictures just don't do justice to the attention to detail from the moment you walk in to this beautiful lakefront homeHost:
all added to the warmth and the charm of this family lake houseThis beautifully furnished home with views of the best lake in the Berkshires- Lake GarfieldRead more reviewsLocation:
The house was perfectly located on beautiful Lake Garfield and fully equipped for a familyOur stay at the Aronson Chalet in beautiful Monterey County in the Berkshires went beyond our expectationsWe enjoyed everything from the fishing boating paddle boarding and endless outdoor adventures in the Berkshires
Beautiful homes to relax in
Monterey is a great place for a short getaway from the city and each one of these amazing accommodations will be great to stay in during your time there. You’re sure to find the perfect place for you and your friends or family to relax and rejuvenate while enjoying your holiday.
Frequently asked questions about Vrbo vacation rentals in Monterey, Massachusetts
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