House holiday rentals in Roxbury

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Popular amenities for Roxbury house rentals

House rentals with a pool

Superhost
Home in Woodbury
4.95 out of 5 average rating, 19 reviews

2 homes in one (in-law design) w/salt water pool

ChristineRating, 5 stars9 months ago
Julie is an outstanding host! This house is perfect for any getaway. It was clean, spacious, well equipped, comfortable, and STUNNING outdoor area with a gorgeous pool. This is 3 FULL baths and 1/2 bath!! Two kitchens! Two family rooms! You had space! It made you want to relax! The kitchen was well stocked with any utensil or appliance you would need. It was private. You could really escape and get away. Woodbury and the surrounding towns were jampacked with things to do. There were many places to choose from to eat. Such a variety from steak, seafood, pizza, and American fare pubs and other specialty restaurants. Lots of variety/antique shops, flea market, wine/liquor stores, convenience stores. Just a short drive into Southbury you find more shops, antiques, restaurants, bigger, grocery store, etc. We also drove to a few other neighboring towns. All under 45 minutes. Friendly people! We had a wonderful time! Price is fabulous, house/outdoor area is A+ value! Thank you Julie!!
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.
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.
Top Guest favourite
Home in Cheshire
5 out of 5 average rating, 135 reviews

Pool House

CindyRating, 5 stars1 month ago
The pool house is so cute and the outdoor patio is gorgeous and the perfect place to relax. Great place to stay if you want to stay near New Haven but also want to enjoy quiet away from the city. Sue is a responsive and very generous host!
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 Kent
4.96 out of 5 average rating, 28 reviews

Country retreat on 4 private acres

LloydRating, 5 stars1 week ago
My family and I had such a wonderful time. The home and the surroundings were so beautiful, peaceful, quiet, and relaxing. Everything was very clean, and the bed and pillows were so comfortable. My toddler especially enjoyed the cute bathtub in the master bedroom. The pool was beautiful, just wished we were there when the weather was nicer, as the water was quite cold. The restaurants nearby (10 mins away) were so good, we especially loved everything from a place called Kingsley Tavern. Overall, loved our stay and would definitely stay here again!
Guest favourite
Home in Redding
4.88 out of 5 average rating, 16 reviews

Meeker Hill House - Country Escape w/ Heated Pool

RoryRating, 5 stars8 months ago
Our stay was stunning. The location is quiet and peaceful yet close enough to the town to get what you may need. The home itself is absolutely gorgeous. It’s clean, the layout is beautiful, and the views are out of this world. A truly incredible place to stay. The beds were very comfortable, the kitchen was perfect, and each room has a full bath which was great for our family. Overall highly recommend

Weekly house rentals

Top Guest favourite
Home in New Milford
4.97 out of 5 average rating, 31 reviews

OWL's PERCH Candlewood Lakefront Rustic Cottage!

JackieRating, 5 stars1 week ago
If you're looking for a cute little cottage in the woods near the lake to recharge and relax - this is it! KC provided an extensive list of instructions and to know's, which made check in/check out and all the in-between fool proof. KC was super friendly and responsive as well!
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!
Top Guest favourite
Home in Danbury
4.98 out of 5 average rating, 96 reviews

Lakeview Estate - Chef's Kitchen - NYC Getaway

AizelRating, 5 stars2 months 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 Newtown
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
Guest favourite
Home in New Fairfield
4.97 out of 5 average rating, 75 reviews

Hilltop Retreat- Lakefront with Dock

JoeRating, 5 stars2 months ago
Our stay included spending family time in front of the fireplace watching Disney shows and with time spent enjoying meals around the cozy kitchen table. Enjoyed our stay very much and hope to go back one day
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 Washington
4.96 out of 5 average rating, 55 reviews

Lake View Cottage

KatieRating, 5 stars3 weeks ago
Enjoyed staying 4 nights. The house is beautifully designed and decorated with lots of natural light. Great location across the street from the Lake and walking distance to New Preston shops, coffee and restaurants. Enjoyed daily morning walks around the Lake. David was a great host- responds within minutes, easy check-in and check out. Highly recommend.
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!

Private house rentals

Guest favourite
Home in Branford
4.97 out of 5 average rating, 36 reviews

Adorable Beach House on LI Sound

LisaRating, 5 stars1 day ago
There’s so much to love about this charming open plan beach cottage! We especially enjoyed the water views, hearing the birds, and eating on the breezy porch. It was sparkling clean and stocked with everything you’d need, from comfortable beds and towels to many thoughtful essentials like hand and dish soaps, tea and coffee pods, paper towels/toilet paper, and shampoo/conditioner. Eileen is a gracious and responsive host — she was particularly understanding when we had to reschedule our visit. Thank you for a wonderful stay, Eileen, and we hope to return!
Top Guest favourite
Home in Plymouth
4.98 out of 5 average rating, 44 reviews

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

WilRating, 5 stars1 day ago
Shawn created a special place here. Love all the details, especially the skateboards and music room. The hot tub was lovely after a long day of driving, I soaked again in the morning. ColecoVision console in the game room was so nostalgic along with a great selection of other games. I really enjoyed the grounds. Even wandered down to the dam/waterfall. My mother in law, son and wife all had their own space to stretch out. I could easily spend more time here, it is not just a place to lay your head for the night.
Top Guest favourite
Home in New Fairfield
5 out of 5 average rating, 39 reviews

Candlewood Isle Cabin ~ Dog Friendly~ Lake ~ Dock

AlesiaRating, 5 stars1 month ago
The location suited our needs perfectly. It was close to our Jehovah’s Witness facility in Patterson NY. We had a morning tour which made it very convenient, only 20 minutes away. We not only enjoyed the peaceful quietness, we were also able to do a little fishing at the boat docks right on the property of Candlewood Isle and caught a few fish.☺️
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 stars3 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.
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 Morris
4.98 out of 5 average rating, 48 reviews

UB’s Corner

CatherineRating, 5 stars1 month ago
Our stay at Ellen’s Lake House was perfect. It was comfortable, clean and the view of the lake is amazing. My husband enjoyed fishing and we both loved being on the water. Ellen was helpful and made our stay a wonderful experience.
Guest favourite
Home in Woodbury
4.9 out of 5 average rating, 67 reviews

Historic Country Retreat in Litchfield County

KatherineRating, 5 stars3 months ago
Wonderful home in Woodbury, very quiet road but very near town. Easy drive to both Roxbury and Washington. We enjoyed our time with our pup Birdie, a great yard for playing fetch. We will be back hopefully in the fall.
Top Guest favourite
Home in Brookfield
4.94 out of 5 average rating, 90 reviews

Sleeps 18 LAKE VIEWS! Perfect for large group!

AlexRating, 5 stars6 days ago
Very nice house for a big family (10+ people). Everything we needed as far as utilities, amenities etc. was there. Great view from the deck and lots of parking (enough for 5-6 cars easily). Open floor plan and access through two entrances is very convenient. Liked the place and how everything was set up there. The host is very friendly and responsive.

Destinations to explore