House holiday rentals in Roxbury

Find and book unique houses on Airbnb

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Popular amenities for house rentals in Roxbury

House rentals with a pool

Superhost
Home in Litchfield
4.82 out of 5 average rating, 105 reviews

The Getaway-HOST & Co.

CrystalRating, 5 stars9 months ago
I absolutely enjoyed my weekend here. The home is beautiful. Everything you could possibly need was provided In the home. Everything was clean, and neat. House is filled with light. The pool and hot tub were enjoyable. The host were amazing and had great communication, assisted us when needed right away. I would highly recommend staying here, and they are pet friendly which is always a plus for me. The yard is fenced in. Which made it easy to let the dog out, and great for the dog to explore. A++++ Will probably be back sometime In the future.
Top guest favourite
Home in Monroe
4.97 out of 5 average rating, 201 reviews

Garden Level Suite with Beautiful Pool

GraceRating, 5 stars3 months ago
We had an amazing time at Marybeth’s suite—it truly felt like a winter wonderland. Our kids had a blast "swimming" in the snow and "rolling" over the gentle hills. Every moment was filled with joy, whether we were relaxing in the sunroom, playing in the snow, or swinging outside. The time spent together as a family, along with our conversations with Marybeth and her family, was truly precious. We can’t wait to return in the summer!
Guest favourite
Home in Rhinebeck
4.89 out of 5 average rating, 144 reviews

4Br Mountain Brook House on 130 acres w/ trails

AnnetteRating, 5 stars2 weeks ago
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.
Guest favourite
Home in Stamford
4.96 out of 5 average rating, 251 reviews

Midcentury Modern ZenHouse Sculptor Studio

EamonRating, 5 stars1 week ago
Truly one of a kind property. Relaxing, calm, extremely responsive and helpful host. If you are looking to get out of the city or just need some time away to think, look no further. 10/10.
Top guest favourite
Home in North Fork
4.97 out of 5 average rating, 154 reviews

Secluded Farmhouse - Studio Apartment Style Unit

JosephRating, 5 stars1 week ago
Great location, private and comfortable. Close to wineries and breweries. Very clean and convenient. I highly recommend.
Top guest favourite
Home in Pound Ridge
5 out of 5 average rating, 163 reviews

Peaceful Light-Filled Guesthouse 1 Hour From NYC

MollieRating, 5 stars3 weeks ago
Obsessed with this Airbnb! My husband, dog and I typically go to upstate NY or the Berkshires for long weekends but I came across this Airbnb as I had an event in westchester over the long weekend. Highly recommend! So much hiking, wonderful restaurants and so close to the city. My dog loved this property as well! Will be back.
Guest favourite
Home in Litchfield
4.93 out of 5 average rating, 190 reviews

Stunning Views, Bucolic Bliss in 1790s Farmhouse

PaulRating, 5 stars2 days ago
We really enjoyed our time at Elizabeth Jane's place. The home is spacious and quaint, with nice furnishings, a tasteful colonial feel and easy access to downtown Litchfield and the Berkshires. The bucolic setting is lovely - scenic, relaxing and peaceful.
Superhost
Home in Beacon
4.92 out of 5 average rating, 133 reviews

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town

MarissaRating, 5 stars2 weeks ago
We had a great stay at Tiffany’s place! Everything was exactly as described and she was great at communicating throughout the stay.

Weekly house rentals

Guest favourite
Home in Pleasant Valley
5 out of 5 average rating, 27 reviews

The Wildflower House

MatthewRating, 5 stars1 month ago
Loved every part of our stay with Kristine. Perfect for a romantic weekend away - gorgeous cabin, well appointed, and great kitchen for cooking-in. Her recommendations for local spots were also so thoughtful. Thank you again!
Guest favourite
Home in Woodbury
4.94 out of 5 average rating, 97 reviews

Ferris House: Private 19th Century Home

BethRating, 5 stars5 months ago
From the moment we drove up it felt like we were on a movie set! It was the Christmas season and the entire home was decorated with lights, trees, and wreaths....absolutely stunning. Did I mention the extended property? WOW...breathtaking!! William met us and showed us around Ferris House, which he took great pride in. Every corner of every room is so special. We celebrated Christmas with our Connecticut family and they all agreed....the home was cozy and perfect. The beds were comfortable, the house temperature was just right (it was winter after all), gorgeous furnishings everywhere, the kitchen fully stocked with dishes, utensils, pots and pans, lots of hot water for showers (we were 4 adults) plus the best espresso maker! We are in Connecticut quite often and this will be our new home away from home! Can't wait to come back.
Top guest favourite
Home in Danbury
4.98 out of 5 average rating, 96 reviews

Lakeview Estate - Chef's Kitchen - NYC Getaway

AizelRating, 5 stars1 month ago
This house was wonderful as I would definitely stay there again and recommend it to family and friends. The views from the balconies and windows were amazing! The house was absolutely beautiful and super clean. The location was secluded but still near shops and restaurants. We loved our stay!
Superhost
Home in Sandy Hook
4.86 out of 5 average rating, 7 reviews

Serenity by Lakefront Cottage!

LuisRating, 5 stars3 weeks ago
Definitely recommend will be there another time thanks
Top guest favourite
Home in Newtown
5 out of 5 average rating, 16 reviews

A nestled retreat on 15 acres

SusanRating, 5 stars1 week ago
We loved this house, it's beautiful inside and out. We watched deer in the early morning and had a dozen or more flowering trees dotting our view. The house is immaculate, and the kitchen is a dream for prepping and cooking. We were able to visit Yale, ocean beaches, wonderful restaurants, and ran into two farmers markets full with welcoming artists.. we had a rainy evening and enjoyed listening to the rain while we read. It's a great location if you want to do a Gilmore Girls weekend. If you know, you know. Thank you Kathleen for sharing your home.
Top guest favourite
Home in Sharon
5 out of 5 average rating, 28 reviews

Nature lover’s retreat in NWCT, breathtaking views

ScottRating, 5 stars5 months ago
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!
Top guest favourite
Home in Newtown
4.99 out of 5 average rating, 96 reviews

Comfortable home away from home

AaronRating, 5 stars1 week ago
Terry and Jack’s place was perfect for us staying in Newtown visiting friends but we could also drive to Manhattan for day trips. House had everything you’d need and they even helped us get a crib delivered early/picked up later after we left. Super nice and responsive hosts! Will definitely stay again!
Guest favourite
Home in Trumbull
4.97 out of 5 average rating, 32 reviews

Cozy studio quiet and safe

GustavoRating, 5 stars2 weeks ago
amazing place to stay at while in CT. close enough by the big areas, while being in a very quite neighborhood. clean house with a cozy vibe to make you feel at home. while small, the space provided was enough for 2 people and really comfortable. host was fast to respond to messages and was extremely kind. overall 10/10 experience and will recommend to anyone looking for a nice place to stay for a good price.

Private house rentals

Top guest favourite
Home in Plymouth
4.98 out of 5 average rating, 42 reviews

Don’t miss out on this cozy escape! w/Skatepark

ChristopherRating, 5 stars3 days ago
Would gladly stay here again. Shawn was responsive and the place had everything we needed. Hope to come back to this part of CT again
Guest favourite
Home in Holmes
4.91 out of 5 average rating, 11 reviews

Enchanted Escape | POOL, LAKE, Concierge Services

AnxhelaRating, 5 stars2 weeks ago
We had such a great experience staying at this Airbnb. The house was beautiful, super clean, and the view was just perfect honestly even better than the photos. What really made our stay stand out though was the host, Sunny. He was amazing so helpful, kind, and incredibly thoughtful. As a Muslim family, we really appreciated how respectful and considerate he was. He made sure we had our privacy and went out of his way to make everything as easy and comfortable as possible for us. It honestly felt like staying at a friend’s place. We’d definitely come back and highly recommend this spot to anyone looking for a peaceful, welcoming place to stay.
Guest favourite
Home in New Milford
4.95 out of 5 average rating, 21 reviews

Spacious and relaxing New Milford 5br home w pool!

ElizabethRating, 5 stars6 months ago
Jarret was extremely helpful and friendly. The house was exactly what we needed. I will definitely come back and stay here next time I’m in town.
Guest favourite
Home in Warren
5 out of 5 average rating, 16 reviews

Magical Woodland Getaway

KayRating, 5 stars2 months ago
Lovely home, beautifully decorated, in great country setting with easy access to neighboring towns. Our host was very responsive.
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 stars2 weeks 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.
Guest favourite
Home in Woodbury
4.89 out of 5 average rating, 66 reviews

Historic Country Retreat in Litchfield County

TiffanyRating, 5 stars4 months ago
My family absolutely loved our stay! The home has been beautifully restored and is comfortable and clean. It was the perfect quiet getaway we were hoping for, while being close to all conveniences such as grocery stores, restaurants and coffee shops.
Top guest favourite
Home in Warren
5 out of 5 average rating, 50 reviews

Moody Pond House: Weekend Country Escape

KatieRating, 5 stars1 month ago
We stayed 4 nights at the Moody House. Description of the house was perfect- check-in was seamless. We loved all the natural lighting in the house. Even with a lot of rain, we enjoyed the views of the backyard and quiet area. We didn’t use the hot tub but was provided a video on how to use. Jessica and Adrian provided a great list of shops, grocery stores and restaurants- which we used, so much appreciated! Highly recommend this Airbnb.

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