House holiday rentals in Southwick

Find and book unique houses on Airbnb

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Popular amenities for Southwick house rentals

House rentals with a pool

Superhost
Home in Stonington
4.9 out of 5 average rating, 105 reviews

Homestead Near Mystic, Casinos & Beaches

Sherri Watson Rating, 5 stars1 month ago
This was the perfect spot for what we were looking for as my son graduated from Conn College. The host was very responsive to my questions and flexible with check in times which we needed. House was exactly what was described and we had a wonderful time. Thank you!!
Guest favourite
Home in Montville
4.92 out of 5 average rating, 273 reviews

Casino Wine Down House

EsperanzaRating, 5 stars1 week ago
Beautiful, relaxing, clean Airbnb. Had an issue with the shower, which can happen anywhere, Mk was super responsive and came over quickly. Loved loved loved our stay here. Didn’t use the swimming pool due to weather but the screened deck with the Fire Pit and the superb game room saved the day. Thank you for hosting us will be back
Guest favourite
Home in Colrain
4.9 out of 5 average rating, 129 reviews

The 1770 House

CatherineRating, 5 stars1 month ago
Historic house on a beautiful property. Kitchen had all the equipment you could need along with top of the line stove and oven. Make cooking for a large group easy and enjoyable!
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 Westhampton
5 out of 5 average rating, 27 reviews

Happy Valley getaway

ChrisRating, 5 stars1 week ago
We had a wonderful stay in Westhampton. The place itself had plenty to do and was well stocked with amenities. The owners were also very proactive in letting us know about an issue with the previous renters that resulted in a deeper cleaning than expected. Nevertheless, we recommend Jen’s house and would definitely stay there again.
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 Woodstock
4.94 out of 5 average rating, 239 reviews

Cedar Ridge: House or House+Apartment

AlissaRating, 5 stars5 days ago
We LOVED: 1) The location! The driveway is long & sand/gravel but you could drive it in a sedan fine. 2) The amenities! The pack n play was a HUGE lifesaver! 3) This location is mostly child friendly. 4) The view is phenomenal! When we woke up & opened the curtains for the first time, we were in awe! 5) The host was extremely helpful. The hot water went out once, but she was over in 5 minutes to fix it. Some feedback: 1) The windows in the ceiling in the master bed! They're HUGE and BRIGHT. 2) The bugs. Ants. Spiders. It was a struggle. NOW I WILL SAY - I brought this up to the host on day 3 and they were more than willing to come help how they could. The house is located in the middle of the forest, but it was a lot. If it weren't for an m&m left under the nightstand in the bedroom by a previous guest, it probably wouldn't have been so bad. 3) the coffee maker was pretty rough when we got there.. a simple over site by the crew. Overall, I would definitely consider this location again
Superhost
Home in New Hartford
4.79 out of 5 average rating, 42 reviews

Mountaintop Nirvana: Lake, Pool, Hot Tub, Nature

ColleenRating, 5 stars2 weeks ago
We had an amazing stay! David was quick to respond with any questions I had and even came out to hook up the propane tank for the heated pool. I saw in previous reviews about the tricky driveway but David’s description of it is perfectly accurate and not any trouble, just a little steep but nothing super tricky to deal with! The house has a beautiful setup and view, very clean and so much space. Even though it was cold and rainy we had the most fun and peaceful stay at this home. The bride of the bachelorette group said she wants to book with David on her own just for another stay/get-a-way! Highly recommend this beautiful space!

Weekly house rentals

Top Guest favourite
Home in Windsor
4.98 out of 5 average rating, 56 reviews

Relax By The Water

Meera (& Eliot!)Rating, 5 stars1 month ago
Bryan and June’s place is peaceful and cozy, and the location by the river is spectacular. The kitchen was really comfortable, clean and usable with lots of cookware and nice quality dishes to eat off of; we easefully made multiple meals together and really enjoyed doing it - which isn’t always the case with Airbnbs. Both bedrooms are lovely, so if you’re in a group that needs both bedrooms, this is a rare find where EVERYONE gets “the nice room.” A rare find!! The beds are comfy and on the softer side, and should work great for 99% of people (they were just fine for my spouse and for our friend who traveled with us). IF you are someone who needs an especially firm and supportive bed due to back issues (my situation, sigh), they may not work for you. I’m only sharing that for anyone else in my very specific position, since I also rely on reviews for info like this!
Guest favourite
Home in Springfield
4.94 out of 5 average rating, 93 reviews

Clean/Spacious 1 bedroom house. Kitchen, LR, DR.

FeliciaRating, 5 stars2 weeks ago
We really enjoyed our stay here. House was comfy and clean on a beautiful quiet street. Plenty of off road parking. There were little extras throughout the house that was very convenient, although we didn't need it, there were plenty of toiletries and snacks! Maria was an excellent host very attentive to making our stay comfortable as possible.
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.
Guest favourite
Home in Tolland
4.95 out of 5 average rating, 61 reviews

Spacious Home w/ Hot Tub in Private Lake Community

NataliaRating, 5 stars6 days ago
This was our second stay at the house and we will continue to return. Beautiful, clean, well-stocked home and responsive host. Tina even accommodated an early check in and late check out so our trip could go smoothly with baby nap and event schedules. Highly recommend.
Superhost
Home in Ellington
4.8 out of 5 average rating, 66 reviews

Cheerful 3 bedroom home with large back yard

Olga MariaRating, 5 stars1 week ago
Mr. Andrew was great! Made sure we didn't go without. On my next trip I would LOVE to come back. I felt right at home.
Guest favourite
Home in Windsor
4.91 out of 5 average rating, 46 reviews

Quiet Comfy Getaway 3 BDR home

RandyRating, 5 stars1 week ago
We stayed at Drene’s place for a wedding weekend with a couple of friends. Everyone really felt at home and we loved the place. We even extended for an additional day. Her kitchen had everything we needed to prepare something for ourselves, and the building is in a very calm neighborhood. We would stay there again whenever we’re in town.
Guest favourite
Home in Northampton
4.92 out of 5 average rating, 39 reviews

The Walnut Apartment

JuliaRating, 5 stars1 week ago
Very cute apartment and more than what we needed for a one night stay on a wedding weekend! The downstairs has a charming sitting room and spacious kitchen with fridge, stove, and laundry. The stairs were a bit steep so be cautious! Upstairs a comfy soft bed with window AC and a large bathroom with clawfoot tub/shower. Jennifer was very nice about our last minute request to check in early to change for a 4 PM wedding. We would stay here again if we come back to the area! Thanks so much!
Guest favourite
Home in Springfield
4.93 out of 5 average rating, 46 reviews

Quiet 2 Bedroom - near Big E, Massmutual, Six Flag

CarrollRating, 5 stars1 week ago
Comfortable two BR unit perfect for our needs. Bottom floor of two-story home, Perfect for two adults. I was in town to participate in IM 70.3 race, and it had all the basics needed for two. Located near Forest Park, a nice little urban park that even has a little zoo. Would definitely stay here again.

Private house rentals

Top Guest favourite
Home in Hillsdale
5 out of 5 average rating, 51 reviews

Cambridge Hill Farmhouse - Sauna - Swimming Pond

janetRating, 5 stars1 week ago
This was a perfect vacation home for our family trip. Spacious house with beautiful indoor and outdoor spaces, a well equipped kitchen, luxurious and extremely comfortable furnishings and a location that makes visits to surrounding charming towns so easy.
Top Guest favourite
Home in Windsor
5 out of 5 average rating, 40 reviews

By The River

EhiraRating, 5 stars1 month ago
Peaceful place. It looked like the photos. The communication was clear and quick respond. Easy access
Guest favourite
Home in Enfield
4.95 out of 5 average rating, 62 reviews

Cozy First Floor Living Nestled in the Woods

ErikaRating, 5 stars4 weeks ago
We loved our stay in Stacy’s cozy, clean, and pet-friendly home! Our furbaby felt right at home and enjoyed the dog toys. Host was responsive and accommodating. Peaceful, and very beautiful home in a nice area. Highly recommend!
Guest favourite
Home in Springfield
5 out of 5 average rating, 10 reviews

VDM Property!

SusanneRating, 5 stars2 weeks ago
Clean, quiet, and comfortable place. Perfect location for a short drive everyday to Northampton for a sporting event I was competing in. Minutes from the highway and a coffee shop just a two minute drive from the house. Perfect for a quick, easy start to early mornings.
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!
Guest favourite
Home in Sandisfield
4.96 out of 5 average rating, 73 reviews

Lux on the River near Tanglewood w/220v EV charge

AnnaRating, 5 stars1 month ago
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.
Superhost
Home in Blandford
4.84 out of 5 average rating, 76 reviews

Relaxing Home nestled in Rural Hilltown

MichaelRating, 5 stars1 week ago
My son, his dog and I had a lovely weekend of hiking and hanging out. The accomodations were excellent and we were close to many hiking trails and about 20 minutes away from Westfield and 45 minutes away from Northampton. The house was very comfortable and functional. Great TV room for watching sports and movies. Two bedrooms and two bathrooms. Perfect for our needs.
Superhost
Home in Enfield
4.78 out of 5 average rating, 32 reviews

RiverView Oasis

AnnRating, 5 stars6 days ago
A couple of snafus were handily dealt with by Akudo, who is very responsive. The bed were comfy and the view is outstanding! It took no time at all to acclimate to the friendly rumbling trains speeding by. A nice place to stay.

Destinations to explore