
House holiday rentals in Monterey
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Top-rated house rentals in Monterey
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Popular amenities for house rentals in Monterey
House rentals with a pool

Berkshires Oasis Retreat: Art Meets Nature
We had a lovely time with our family! We were with 2 young children and my elderly father who cannot walk well (uses a walker). The house was perfectly designed to accommodate my father and had great living areas for us to spend time together. A very cozy, warm and welcoming home (with lots of amenities!). Yael is a very friendly, responsive host. We’d gladly come back for another winter or perhaps a summer stay! Thank you Yael!

midcentury mod * POOL * walk out trail to mohonk
The house met all expectations everything is stylishly done, and the host is incredibly responsive and helpful 🤍

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres
Very enjoyable time here! Instructions, accommodations, and overall experience was perfect!

Scenic River View Escape | New Paltz
I spent my birthday at this beautiful house and couldn’t have asked for a better experience. The place was spotless and full of natural light, with lovely views that made the stay even more special. The atmosphere was peaceful and clean, and the house had everything we needed for cooking and relaxing. I truly felt at home and appreciated all the thoughtful touches. Highly recommend for anyone looking for a cozy, well-equipped getaway!

4Br Mountain Brook House on 130 acres w/ trails
It was a fantastic house with a beautiful view. Plenty of space and we really enjoyed our stay. The property itself is absolutely gorgeous. Would definitely come back.

Stunning luxury home with pool
Beautiful home! Extremely clean upon arrival and excellent communication. Everything in the house was clearly labeled and directions for check-in and check-out were very clear. Sadly it rained our entire stay so we could not enjoy the pool or the beautiful backyard, but we still had a lovely stay. We hope to come back soon!

Modern Barn on 12 acres w Sauna, FirePit+swimming
Cozy home, on a beautiful property. The natural pool is really special, and we loved staying here. Hope to be back.

Upstate Modern Scandinavian Barn in the Catskills
We truly enjoyed our stay at Wilderkill Barn. Maria Cristina and William were exceptional hosts—warm, attentive, and genuinely committed to making our visit special. They went above and beyond to make us feel welcome. The home was a haven, with a hot tub, sauna, pool, fire pit, pool table, and immersive sound and movie systems—all of which made our stay delightful despite the cold, dreary May weather. We can't thank them enough. ***That said, we feel it's necessary to address a serious issue with Airbnb itself that arose while booking this property, unrelated to the property itself. An unexpected tax was added after booking, and Airbnb has yet to provide a clear explanation. After years of loyalty, we were disappointed by their evasive and unhelpful customer support. This experience has made us reconsider using the platform in the future. We urge potential users to scrutinize all fees carefully and be aware that Airbnb’s support may be difficult to navigate if problems arise.***
Weekly house rentals

Nerd Preservation Sanctuary
My husband and I loved our stay at this house. It checked all our boxes. It was clean, spacious, had a comfortable bed, plenty of hot water and a barbecue grill. It also came with lots of personality. We ate breakfast at the local country store/cafe called Sherwood Forest most days. It was a great place to relax and enjoy the peaceful surroundings.

Cozy Berkshire Getaway
We were happy with this AirBNB and would stay here again. It was nice and quiet but a very short drive into Great Barrington. Close to lots of hiking. Updates have been made since some of the previous reviews. There are two couches in the living room and some of the stock items in the kitchen for convenience.

Waterfront oasis in heart of Berkshires
The location was peaceful and beautiful with great local restaurants, farms, and hiking. The reservoir was a nice amenity with the kayaks and canoe. The house was well maintained and comfortable with pretty views on the first floor. We enjoyed our stay

Fickle Fox Farm. Spring in the air, Summer is soon
Staying at Amanda and Andrew’s place in Canaan, CT is an exceptional airbnb experience. The home and property are in excellent condition, exactly as pictured in the airbnb profile . And, Amanda and Andrew are quintessential hosts, friendly and responsive. We cannot recommend staying here highly enough. Thank you Amanda & Andrew !

Hudson Riverfront Mid-Century Modern Home
A beautiful, comfortable house right on the Hudson with stunning views. We loved watching all the life on the river, herons and loons and ducks, as well as boats from tiny crafts to massive barges. There are great hikes just a short distance away. It is a perfect place to rest, write, draw, and make music.

Nature lover’s retreat in NWCT, breathtaking views
Kellen and Samantha's home and property are very special--a wonderful location for a restful retreat in nature that is also a short drive to several charming towns in northwest Connecticut. The hilltop site offers breathtaking views of surrounding mountains, valleys, and forest. The residence sits atop a long driveway off a gravel road so is serenely quiet and private. Inside, the space was immaculate, thoughtfully designed, and very comfortably furnished. The shower, bed, towels, and linens were all particularly fantastic, as was the full kitchen which allowed us to cook nightly. The area is exceptional for hiking, culinary delights, and all sorts of shops. And our hosts were proactive, helpful, and clear in all of their communications. We really loved staying here, as did our dog, and we hope to return. Highly recommended!

Berkshires! Canoe Use, HOT TUB, Private
Memorable stay in The Berkshires! Nicole's place was cozy and welcoming a great place to relax and unwind after long days of sightseeing and shopping. At night the backyard would be lit by the soft glow of string lights and made for the perfect scene to end every day in the hot tub.

Serene home in the Berkshires
This was perfect for a fall weekend getaway in the Berkshires! Very comfortable and clean. Easy drive to other towns we wanted to explore including Lee and Lenox. Highly recommend!
Private house rentals

Private Retreat: Hot Tub! Movie Room! Pool Table!
We had a wonderful time and this house is completely amazing. There is absolutely nothing missing! When Tiffany said, "all you need to bring are clothes" she wasn't joking. The person who designed the house was a genius with the master bedroom on one side of the house, the 2nd bedroom on the other side and the 3rd on the 2nd floor. Privacy inside as well as outside. It was a hiking trip for the family and included Kennedy Park, Olivia Outlook and the Great Monument Mountain. After spending the day hiking, the hot tub, playing pool and watching a movie in the theater just ended a perfect day. We didn't realize how close we were to MA and it was bonus to explore Western Mass as well. Thank you Tiffany for sharing your home with us.

NEW! Berkshires Farmhouse w/ Firepit & Wood Stove
We had a wonderful stay at James and Lissy’s house! It was perfectly located for getting around the Berkshires. The house was clean, beautiful, and cozy. When we needed to communicate with James and Lissy they were incredibly responsive and helpful. Every year, my friends from high school and I meet up for a reunion in the Berkshires (we have been doing this annually), and the hope is to stay in this very Airbnb next year, if possible/ available! It was an exceptional Airbnb experience!

Greystone at Twin Lakes
The house was even more beautiful and quaint than the photos. The weather was a bit chilly and they made sure the heat was on prior to our arrival. Caring, responsive, and helpful hosts. Definitely recommend.

Charming Cottage - Walk To Town
Perfect location for a few friends that came for a birthday party. Was perfect. I didn’t worry about them at all, and I knew they had a quality stay

Berkshires Lakefront Stylish Retreat w/Gameroom
What an amazing stay. The house is right on a peaceful pond and our kids had the best time exploring every day by canoe. We saw foxes, beavers, tons of birds, and ended each day with s’mores by the fire. Total magic! The house itself was super comfortable and had everything we needed. And the full-size arcade machines were a huge hit with the kids! We’d come back in a heartbeat!

Lux on the River near Tanglewood w/220v EV charge
This is a great stay! Peaceful and you feel as if You are one with nature. Very clean. Arthur and Julie are quick to respond. Kitchen and bath have everything you need, including starter and wood for the wood stove. Cozy place right on the river where you can listen to the rolling sound of the river. Close to CT where we had a nice dinner at an old Inn with delicious blueberry cobbler. Beautiful Drive to norman rockwell museum, great Barrington and other Berkshire towns. We would most definitely stay at this home again.

NEW! Hilltop Ski and Sun Chalet with Hot Tub
Such a perfect house and a perfect stay! We did a midweek stay just to relax and couldn’t have had a better place to do so! The house is beautiful and so clean. The kitchen and everything you need to cook or grill (or make cheeseboards which is what we did). It’s super private and quiet and the back porch is the best. We loved having coffee on the porch every morning. Very close to downtown GB and plenty to do and see! Clear instructions and details about everything in the house and we got to check-in a little bit early. Hope to stay again!

Stylish Rural Sanctuary with POOL!
A truly amazing experience. I wholeheartedly recommend staying at Amanda & John’s home. You won’t find a better, more cared for, more beautifully appointed home. Everything you could ask for and more. Super kind, responsive hosts and every detail is considered. Great WiFi, too. If you’re looking for an experience in a spacious landscape, in quietude, with stars up above, this is the place.
Quick stats about house rentals in Monterey
Total rentals
50 properties
Nightly prices starting at
₹12,116 before taxes and fees
Total number of reviews
2.3K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
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- Six Flags New England
- TPC River Highlands
- Albany Center Gallery
- Bushnell Park
- Jiminy Peak Mountain Resort
- Taconic State Park
- Berkshire East Mountain Resort
- Catamount Mountain Ski Resort
- Zoom Flume
- Kent Falls State Park
- Walkway Over the Hudson State Historic Park
- Bash Bish Falls State Park
- Mount Greylock Ski Club
- Norman Rockwell Museum
- Dinosaur State Park
- Mohawk Mountain Ski Area
- Beartown State Forest
- Hartford Golf Club
- Bright Nights at Forest Park
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Opus 40
- Naumkeag
- Country Club of Waterbury