House vacation rentals in Southwick

Find and book unique houses on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Southwick house rentals

House rentals with a pool

Guest favorite
A saltwater pool features a vibrant blue surface and is surrounded by a spacious terrace. Sun loungers are positioned along the poolside, and a fenced area provides safety. Lush greenery creates a serene backdrop, enhancing the outdoor space for relaxation.
Home in Woodbury
4.94 out of 5 average rating, 18 reviews

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

ChristineRating, 5 stars7 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 Egremont
5 out of 5 average rating, 4 reviews

Exquisite family friendly home with heated pool!

AmyRating, 5 stars10 months ago
We had a wonderful family vacation staying at Stone Hill. The house is absolutely perfect, literally a dream house. The pool and landscaping are beautiful and peaceful. The kitchen has everything you could ever need for cooking big meals. We thoroughly enjoyed the basket with s’mores ingredients and the fire pit. The screened-in porch was the perfect spot to enjoy morning coffee and look out at the scenery and pool. The ping-pong table in the basement was fun for the whole family, as well as a great selection of games and cards in the TV room. These came in handy on our 2 rainy days. The owner was super responsive to a few questions we had. It’s the perfect location, only a short drive to Great Barrington and grocery shopping at Guido’s. There’s also a great dog park in GB if you’re traveling with a dog. We hope to come back to Stone Hill many times in the future.
Guest favorite
A spacious outdoor area is visible, featuring a winding path that leads through a grassy landscape. Trees of varying heights frame the view, capturing seasonal colors with a backdrop of rolling hills under a clear blue sky.
Home in New Milford
4.94 out of 5 average rating, 32 reviews

Serene Country home 24 mi Mohawk ski area

ConnieRating, 5 stars1 month ago
A beautiful home- super comfortable and spacious. It is outfitted with everything you could need. Peaceful location (we stayed in spring/winter- can’t speak to what it would be like in season). Lovely views. Easy to get into town by car (3-5 minutes!). Host was excellent - responsive to any questions or inquiries
Guest favorite
A heated pool is surrounded by a spacious, patio area featuring lounge chairs and a shaded table set, providing a relaxing outdoor space. Lush greenery and fencing enhance privacy, while a comfortable seating area can be seen beyond the pool.
Home in Litchfield
4.99 out of 5 average rating, 84 reviews

Hilltop House w/POOL/SPA- HOST & Co.

DanielRating, 5 stars2 months ago
Great house and great host. The place was beautiful -- big kitchen, comfortable bedrooms, great bathrooms (especially in the master bedroom), nice setup outside (jacuzzi and BBQ), etc. Perfect place for a family weekend in Litchfield. Location was perfect -- a 2 minute drive to great coffee, pastries, bread, ice cream, etc. in Bantam. Liz was an excellent host -- very helpful and responsive. We'd love to visit again soon.
Top guest favorite
A neutral-toned hallway with warm wooden flooring is shown, leading to a sunlit space at the end. A stylish chair is positioned near a floor-to-ceiling window, allowing natural light to fill the area. Multiple doors line the sides of the hallway.
Home in Roxbury
5 out of 5 average rating, 17 reviews

Bright Mid-Century Modern Retreat-90 min from NYC

SidRating, 5 stars2 months ago
My family and I had a wonderful weekend at the house. The house is beautiful and was extremely clean when we arrived. Luiz kindly left a sled for my kids to use in the yard. There is plenty of outdoor space and the yard has a good deal of privacy. There are two bedrooms and a den/office with a TV. The kitchen has everything we needed. Luiz was very easy to communicate with.
Guest favorite
Home in East Chatham
4.9 out of 5 average rating, 20 reviews

10 Acre Country Estate with Pool, Hot Tub & Views!

DeborahRating, 5 stars1 month ago
We loved staying here with our family. It worked out perfectly having our daughter’s family on the one side of the house so if the baby cried it wouldn’t wake anyone up. A pack and play was also provided by Justin so we had a place for the baby downstairs as well. The house was roomy and comfortable for everyone. The hot tub wasn’t working right away but they let us know and had it fixed so we were able to use it during our trip. We would definitely stay here again and try it in warmer weather so we could use the pool as well. Thank you for a wonderful place to stay
Superhost
The exterior of a Dutch Colonial home is showcased, featuring a red front door and beautifully landscaped surroundings. Bicycles are positioned beside a stone wall, while manicured grass and vibrant flowers line the entryway. Tall trees enhance the tranquil setting.
Home in Washington
5 out of 5 average rating, 6 reviews

ShrinkMapBestTown Washington Calhoun5BR PoshPadsCT

CaryRating, 5 stars20 months ago
The view from the back porch is even more beautiful than you would realize from the images on AirBNB. This is a lovely house in a tranquil, breathtaking location!
Guest favorite
A cozy living room features exposed wooden beams and warm wood-paneled walls. A stone fireplace is centrally located, with a basket of wood beside it. A rug with rich colors lays under a wooden table, surrounded by comfortable seating, inviting a relaxed atmosphere.
Home in Litchfield
4.93 out of 5 average rating, 185 reviews

Stunning Views, Bucolic Bliss in 1790s Farmhouse

TessaRating, 5 stars2 weeks ago
This wonderful antique home is in a Beautiful spot in the heart of Litchfield CT, and a delight early spring when the fields of daffodils awake! This unique 1793 house has a great view & sunset, fireplace, simple spa/gym making it a gem even when the pool is closed. Nearby the town with lots to offer and local farms for food shopping too. What’s not to love 💛 Bonus is a great host offering a home that is in touch with the realities of rentals, pets and people -not picky, precious or punitive. Happy to recommend and return! Thank you Elizabeth!

Weekly house rentals

Top guest favorite
A spacious home is set on a lush green lawn, with a welcoming porch and multiple gabled roofs. The exterior is painted in neutral tones, and a garage is visible on the left. Large windows allow natural light to illuminate the interior.
Home in Stockbridge
4.93 out of 5 average rating, 41 reviews

Stockbridge Cape Near Tanglewood!

MarkRating, 5 stars4 months ago
Very nice accommodations in a great location. A vehicle needed to get around to plentiful hiking, shops in nearby towns, and cultural sites. Very nice home for family gatherings and with all necessary amenities.
Top guest favorite
The entrance features a white wooden façade with two prominent columns flanking the door. A small table and chair set is positioned on the porch, surrounded by neatly kept greenery and a vibrant flowerbed.
Home in Northampton
4.94 out of 5 average rating, 183 reviews

Historic Williams House

JillRating, 5 stars2 weeks ago
This was an utterly charming old house! We loved it. Note that the staircase in the pictures is that narrow – it can be tough for people with mobility issues to navigate. The decorations of the house and the preservation of some of the original construction, make it full of character, a delight to stay in. The host was responsive and very friendly.
Superhost
A charming two-story wooden house is surrounded by lush greenery and colorful flower beds. The exterior features large windows, a balcony on the upper level, and a screened-in porch attached, providing a welcoming entrance set on a quiet country road.
Home in Canaan
4.96 out of 5 average rating, 72 reviews

Peaceful Berkshire Getaway (A/C, Lake Access)

PaulRating, 5 stars9 months ago
Becky’s house was exactly as listed with plenty of space to relax and enjoy the area. Her gardens are beautiful and the house is convenient to the Berkshires without the stress of the downtown areas. We are extremely appreciative of all that was provided!
Guest favorite
A two-story house features light yellow siding with blue shutters around the windows. The front yard is well-maintained, showcasing green grass and neatly trimmed bushes on either side of the entrance. A concrete driveway runs alongside the home.
Home in Enfield
4.91 out of 5 average rating, 11 reviews

3 bdrm house great neighborhood

J DavidRating, 5 stars11 months ago
Wonderful place for our family to spend the weekend while we attended our daughter's graduation a half hour away in MA. Clean, comfortable, spacious and charming in a quiet neighborhood. Auria provided clear instructions, check in was a breeze, and she was extremely proactive and helpful. She responded immediately to questions and was always cheerful and polite. One of the best Airbnb experiences we have had so far. I can not recommend this highly enough.
Guest favorite
A bright bedroom is presented with a spacious bed, accented by a light-colored comforter. A wooden dresser and a bedside lamp add to the decor. Natural light streams through two windows with light curtains, providing a serene atmosphere.
Home in New Britain
4.89 out of 5 average rating, 104 reviews

5•Star CapeCodStyle Gem with a Bedroom on the Main

ErikaRating, 5 stars2 weeks ago
We had a short stay at Chana‘s place, but everything was perfect for our family. We will definitely book again and recommend to others. Thank you Chana.
Top guest favorite
A two-story brick house features a spacious covered porch adorned with planters and an American flag. The entrance is framed by two white doors and decorative accents. Lush greenery and small statues are placed along the walkway, enhancing the welcoming façade.
Home in Holyoke
4.97 out of 5 average rating, 328 reviews

Explore Holyoke from this charming 3 Bedroom house

VirginiaRating, 5 stars1 day ago
This was a perfect place for us to stay at, the place feels like home. My daughter had so much fun jumping in the backyard and playing around. We had a convening really closed by, and the host was super nice with letting us do our debrief meeting at the house. We super appreciated being able to charge our car over night as well. Great folks!> Thank you.
Guest favorite
A bright living area features a large flat-screen TV mounted on a white console. Two colorful armchairs and a brown leather couch surround a wooden coffee table, all set on a blue area rug. Light streams in through a window, enhancing the cozy atmosphere.
Home in East Hampton
4.92 out of 5 average rating, 93 reviews

Clean private home near Lake Pocotopaug!

CathyRating, 5 stars4 months ago
I highly recommend this property. It was perfect for our Christmas visit with family. The furniture and beds were very comfortable. We truly enjoyed our stay in East Hampton. We will be back!
Guest favorite
A serene bedroom features a spacious bed dressed in soft linens and a colorful quilt. A cozy couch is positioned against the wall, offering a relaxation spot. Natural light is let in through multiple windows, highlighting the light blue paneled walls and white furniture.
Home in Lee
4.97 out of 5 average rating, 99 reviews

Stylish Mid-century Modern Berkshires Cape

LarryRating, 5 stars1 month ago
The home was very clean and as described with everything we needed for our visit. Chris was very clear with his check-in instructions and quickly responsive to questions as we got settled. I would stay here again.

Private house rentals

Top guest favorite
The exterior of the home is presented, showcasing a modern two-story structure. Lush landscaping features vibrant azaleas in purple and pink, with well-maintained shrubs bordering a gravel driveway. A garage is attached to the house, complemented by a serene backdrop of greenery.
Home in Egremont
4.96 out of 5 average rating, 120 reviews

The Berkshires Mountain Terrace LUX Home Sleeps 7

CourtneyRating, 5 stars2 months ago
This was a beautiful and well kept home and was a delight to stay in. Natalia was also a lovely and communicative host. We had no issues and would happily stay there again.
Guest favorite
The exterior of a Victorian house is shown, featuring a distinctive gray shingle facade and multiple gabled roofs. Surrounding greenery, including a bush with red berries, adds color to the scene. A porch with steps can be seen leading to the entrance.
Home in Hartford
4.9 out of 5 average rating, 73 reviews

Renovated & Modern Victorian in Historic West End

JoshuaRating, 5 stars1 month ago
I’ve stayed here a few times. I keep coming back because Antonio is a great host. His house is always convenient, clean and comfortable. Can’t really ask for more!
Superhost
The exterior of a charming two-story house is showcased, featuring a brick facade and a peaked roof. A spacious lawn is visible in front, along with a driveway leading to a garage. Lush trees are present in the background under a clear blue sky.
Home in Amherst
4.72 out of 5 average rating, 29 reviews

Lovely 4 bedrooms home with huge backyard to enjoy

GerogeRating, 5 stars9 months ago
Aung is a very helpful gentleman, after I left my personal stuff in the house he’s still very helpful to get everything back for me!
Guest favorite
A light-filled living area features a sofa adorned with green and textured throw pillows. Two stylish chairs complement a round coffee table, and a large bookshelf showcases a collection of books and decorative items. A vibrant area rug covers the wooden floor.
Home in Monterey
4.97 out of 5 average rating, 34 reviews

Hupi House: A Peaceful, Wooded, Lakeside Sanctuary

GallianeRating, 5 stars2 months ago
This was our second time staying at the Hupi House and loved it. House is perfect for 2 families with kids, super comfortable, spacious and cosy, well equipped and lots of things to do in the area. This time we went skiing at the Butternut resort just 10 mins away and was a great experience. Lucas a very friendly and responsive host.
Guest favorite
A cozy sitting area is framed by wooden beams and features a pair of light-colored armchairs. A small area rug is placed on the light wood floor, while a ladder leads to the lofted space above. A framed image of an animal decorates the wall.
Home in Egremont
4.94 out of 5 average rating, 77 reviews

Modern and Stylish Country Lakeside Cottage

DylanRating, 5 stars2 months ago
fantastic and cozy, nice backyard, well equipped with amenities as well
Guest favorite
A rustic red wooden cabin is set against a backdrop of lush green trees. The structure features a sloped roof and a welcoming front porch with steps leading up to it. The surrounding area includes gravel pathways and picnic tables for outdoor gatherings.
Home in Colebrook
4.96 out of 5 average rating, 74 reviews

Log Cabin sleeps 30 bunk style on 350 acres

RomaricRating, 5 stars7 months ago
Beautiful time, we can't wait to come again.
Guest favorite
The exterior view of the house features a two-level deck with seating areas, surrounded by a green lawn and bordered by trees. The cozy building is complemented by a chimney, creating an inviting outdoor space that connects with nature.
Home in Otis
4.93 out of 5 average rating, 15 reviews

Spacious Lake Front Home

JeanRating, 5 stars4 months ago
Beautiful location in Otis, right on the lake and so peaceful. The house is very spacious and easily accommodated our family ( 7 adults and 2 children). All the windows in the house provided great views of the lake, especially from the deck. Our host Nick was very responsive when we had questions or any concerns. Would be nice to come for a stay during the summer.
Superhost
A modern living area is visible, featuring a light-colored sofa and a round wooden coffee table. Pendant lights hang above a kitchen island, where seating is arranged. Neutral tones with indoor plants enhance the space, while an entry door leads to natural light.
Home in Springfield
5 out of 5 average rating, 8 reviews

VDM Property!

AlinaRating, 5 stars3 months ago
We enjoyed our stay at this property. It was extremely clean! There were basic necessities provided. It also had a cute, fashionable interior design. The shower and bedrooms were nice. We liked the layout of this property. Our only issue was that either the heater in the master bedroom wasn't working, or we couldn't figure out how to use it.

Destinations to explore

  1. Airbnb
  2. United States
  3. Massachusetts
  4. Hampden County
  5. Southwick
  6. House rentals