House holiday rentals in Monterey

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Popular amenities for Monterey house rentals

House rentals with a pool

Guest favourite
Home in Otis
4.92 out of 5 average rating, 12 reviews

Berkshires Oasis Retreat: Art Meets Nature

CharlotteRating, 5 stars5 months ago
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!
Top Guest favourite
Home in Athens
4.95 out of 5 average rating, 140 reviews

Private lakefront home, hot tub & resort amenities

KathrynRating, 5 stars1 week ago
My friends and I spent the long weekend here for my bachelorette, we definitely could not have found a better place! Each room has been decorate with such style and care, everyone was blown away that it was even cuter in person. There was plenty of space for everyone to be comfortable, and the two living spaces were perfect for us to hang out and play games. We were also able to put to use the included kayaks as well at the hot tub, which was perfect for the unexpectedly chilly end to our weekend. Vincent’s instructions were super clear and communicated ahead of time, not to mention, it felt like all of our needs were anticipated with included toiletries and kitchen/bar supplies. The stay was seamless start to finished. We definitely hope to stay here again!
Guest favourite
Home in Hudson
4.96 out of 5 average rating, 156 reviews

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

ChristopherRating, 5 stars2 weeks ago
Very enjoyable time here! Instructions, accommodations, and overall experience was perfect!
Top Guest favourite
Home in Catskill
4.98 out of 5 average rating, 54 reviews

Hudson Valley & Catskill Mountain Views • Hot Tub

AaronRating, 5 stars1 month ago
Really a great time and they were very accommodating and communicative. The view is incredible and very close to great restaurants. We used the hot tub every night. Haha
Guest favourite
Home in Rhinebeck
4.89 out of 5 average rating, 142 reviews

4Br Mountain Brook House on 130 acres w/ trails

DanielaRating, 5 stars2 weeks ago
Rick's House (Hemlock House) was a wonderful getaway! We unfortunately didnt hit the best weather but the house was perfect for a cool and rainy long weekend both indoors and out. The open first floor with huge kitchen was great for hanging out and cooking with alot of cozy nooks to read and relax. There was a lot of various outdoor spaces and decks to lounge on as well and the hot tub was perfect for the cooler cloudy weather. The bedrooms were all comfy and each room having its own bathroom was another plus. We all loved the sounds of the creek and being able to walk around the trails in the back. The House is in a fantastic location - only 10 minutes from Rhinebeck which has everything you need and is great for walking around, shopping and dining. Rick was informative and provided a great guidebook with clear instructions and local resources and recommendations. Thanks for a lovely stay!
Top Guest favourite
Home in Great Barrington
4.99 out of 5 average rating, 72 reviews

Stunning luxury home with pool

StephanieRating, 5 stars1 week ago
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!
Guest favourite
Home in Ghent
4.88 out of 5 average rating, 318 reviews

Modern Barn on 12 acres w Sauna, FirePit+swimming

JasonRating, 5 stars2 weeks ago
Cozy home, on a beautiful property. The natural pool is really special, and we loved staying here. Hope to be back.
Guest favourite
Home in Catskill
4.91 out of 5 average rating, 111 reviews

Pool*Hot Tub*Pirate Ship*Fire Pit*Luxury Farmhouse

EliezerRating, 5 stars2 weeks ago
This property is beautiful! The house and amenities are actually just as nice in real and every detail was so thought out. Arp really has good taste and communicated well throughout our stay.

Weekly house rentals

Guest favourite
Home in Sheffield
4.96 out of 5 average rating, 28 reviews

Bull Hill Bungalow

RotemRating, 5 stars5 days ago
We had a wonderful time at Michelle’s place. The house is spacious and full of charm, nestled in lush greenery that made the stay even more relaxing. Michelle was incredibly friendly and responsive, and we felt right at home.
Superhost
Home in Housatonic
4.76 out of 5 average rating, 92 reviews

Cozy Berkshire Getaway

TashaRating, 5 stars1 month ago
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.
Guest favourite
Home in Great Barrington
4.97 out of 5 average rating, 32 reviews

Charming Cottage - Walk To Town

AmandaRating, 5 stars2 months ago
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
Top Guest favourite
Home in Great Barrington
4.99 out of 5 average rating, 95 reviews

Private Home in The Berkshires (New Hot Tub!)

DanielleRating, 5 stars2 weeks ago
Great stay! This is our second time staying at Bradley’s place and it was exactly the same as last time, in a good way. Place was clean, great neighborhood, very quiet!
Top Guest favourite
Home in Staatsburg
5 out of 5 average rating, 80 reviews

Boulder Tree House

SanjayRating, 5 stars2 days ago
This house was absolutely spectacular. The gorgeous, architectural design highlighted its natural surroundings while providing all the thoughtful comforts of a home away from home. Each window is carefully placed to frame the greenery and let in the perfect amount of light throughout the day. From the steam shower to the towels to the linens, the amenities provided were comparable to those offered at a luxury hotel. The hosts were super responsive and welcoming. We couldn’t recommend it more!
Guest favourite
Home in Lee
4.96 out of 5 average rating, 23 reviews

Secluded Modern Lake House

Vanesa & JoeRating, 5 stars3 weeks ago
We spent a wonderful weekend celebrating my daughter's graduation with our family. The house is beautiful, and Lauren and Blake are extraordinary hosts. I totally recommend this house.
Guest favourite
Home in Sheffield
4.98 out of 5 average rating, 49 reviews

The Kellogg House in the Heart of The Berkshires

RosyRating, 5 stars3 months ago
We stayed at the Kellogg House for 3 nights in February while on a ski trip. The house is as charming as in the pictures! It's very nicely designed and set up! Very very kid friendly! (We had 2 kids, ages 7 and 2.5). It was fully equipped with everything we needed, from crib, kids books and toys, fully equipped kitchen, linens, towels etc. The house was close enough to Butternut Ski and to Great Barrington town, so we were within 10-15 minutes of everything we needed. Sabina and Chase were very easy to communicate with and responsive. Great place to stay in the area!
Top Guest favourite
Home in Lenox
5 out of 5 average rating, 26 reviews

Lakefront Retreat -Private Dock,creek,and Fire pit

LizRating, 5 stars1 month ago
Had a beautiful, relaxing stay with friends at George's place right on the lake. Loved sitting on the deck watching trout swim in the stream and deer passing by. The house is in a perfect location, short drive to both downtown Lenox and Lee. In addition, the house is right down the street from High Lawn farm which makes delicious ice cream and cheese. Can't wait to visit again!

Private house rentals

Top Guest favourite
Home in Canaan
4.96 out of 5 average rating, 54 reviews

Private Retreat: Hot Tub! Movie Room! Pool Table!

MusserRating, 5 stars1 week ago
This was a bit of a last minute decision to come to the Berkshires and I was grateful that Tiffany could accommodate some quick changes. The house is just as described--lots of space, nice setting, pool table was fun (and cool in the basement), and I appreciated that our two dogs could be included. Even though the house is in NY, it is not far from the hiking trails and museums. We would like to come back--a lot more to see and do in this area.
Top Guest favourite
Home in Hillsdale
5 out of 5 average rating, 50 reviews

Cambridge Hill Farmhouse - Sauna - Swimming Pond

RebekahRating, 5 stars2 weeks ago
My stay at Danielle’s was so lovely, the swimming pond was so special and just created a beautiful atmosphere around the backyard. The place itself had so much character in the kitchen was greatly stocked. The sauna was lovely and could not get over the view that it had it was raining for most of my trip, but it didn’t take away from the beauty of the place. We were very grateful for how accommodating Danielle was for our arrival and departure. A heads up for anyone that is over 6 foot you will have to duck your head for every bathroom haha would not stop us from booking again though! Such a real gem!
Top Guest favourite
Home in Sandisfield
5 out of 5 average rating, 33 reviews

Waterfront oasis in heart of Berkshires

LisaRating, 5 stars5 days ago
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
Superhost
Home in Lee
5 out of 5 average rating, 7 reviews

Cabin With a Beautiful Lake View

HumiraRating, 5 stars5 months ago
We stayed at Caroline and Nathaniel’s beautiful home over the winter and celebrated NYE’s. Their house is beautiful and perched on top of the hills overlooking a lake. The view is absolutely stunning in the mornings. The house was well maintained and clean. The hosts were very active in communicating with us where we needed anything or if we needed to be aware of any situations regarding the house. I would definitely stay here again.
Guest favourite
Home in Egremont
4.94 out of 5 average rating, 81 reviews

Modern and Stylish Country Lakeside Cottage

NikiRating, 5 stars2 weeks ago
This was my second time staying at Maureen’s beautiful lakeside home and it surely won’t be my last. It’s the coziest, peaceful and inspiring place. Looking forward to future visits!
Top Guest favourite
Home in Canaan
5 out of 5 average rating, 21 reviews

Fickle Fox Farm. Spring in the air, Summer is soon

BradRating, 5 stars5 months ago
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 !
Top Guest favourite
Home in New Hartford
4.96 out of 5 average rating, 69 reviews

Private Woodland Sanctuary—3 mins to a lake beach!

EmilyRating, 5 stars1 week ago
this place is magical. my sisters and I have stayed here twice now, for her wedding and now for mine. both times the home has been clean and the overall experience has been wonderful.
Guest favourite
Home in Port Ewen
4.93 out of 5 average rating, 27 reviews

Hudson Riverfront Mid-Century Modern Home

KevinRating, 5 stars3 weeks ago
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.

Quick stats about house rentals in Monterey

  • Total rentals

    50 properties

  • Nightly prices starting at

    $233 NZD 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

Destinations to explore