House holiday rentals in Middlesex County

Find and book unique houses on Airbnb

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Popular amenities for house rentals in Middlesex County

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!!
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!
Superhost
Home in East Hampton
4.88 out of 5 average rating, 111 reviews

Modern East Hampton Home w/ Heated Saltwater Pool

MariaRating, 5 stars1 month ago
Beautiful home, very clean, spacious and comfortable to stay with the family. We used the grill on multiple occasions and it was easy to use. The fire pitt was also enjoyable. The kitchen was well stocked, would bring own source of caffeine if you’re picky with your coffee though. Stephen, the host was very responsive and easy to reach when asked questions. The one thing I would recommend is to check in with the host if the pool is available to use prior to booking. Overall a great experience, would stay with them again.
Superhost
Home in East Hampton
4.84 out of 5 average rating, 100 reviews

East Hampton Oasis - Pool and Hot Tub

MaryRating, 5 stars1 week ago
We had the most beautiful weekend stay at Tim’s home! Everything is accurately described and the pool and hot tub were amazing!! All the beds were very comfortable. Was perfect for a 5 girl weekend getaway!! Tim was incredibly communicative and checking in was a breeze. The location is PERFECT in East Hampton!! So many amazing restaurants and bars nearby. 100% will stay here again for my next Hamptons trip. Thank you so much Tim!!
Guest favourite
Home in Montville
4.93 out of 5 average rating, 163 reviews

Hot Tub~Pool~Game Room~Fire Pit~BBQ~Casinos

KacieRating, 5 stars2 weeks ago
We had a great time at AJ's place! The space is very spacious and comfortable, everything was clean, and the backyard was PERFECT for our group. Close to casinos and restaurants. Highly recommend for groups and families!
Guest favourite
Home in Cutchogue
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.
Guest favourite
Home in Litchfield
4.93 out of 5 average rating, 190 reviews

Stunning Views, Bucolic Bliss in 1790s Farmhouse

PaulRating, 5 stars4 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.
Guest favourite
Home in East Hampton
4.93 out of 5 average rating, 154 reviews

Large heated pool, games room, near private beach

BerniceRating, 5 stars5 days ago
The house was perfect for my family. I loved the convenience of the one-floor layout and way it allows views of the pool and deck from the almost everywhere so we could enjoy it even when the weather didn't cooperate and we couldn't swim. The family /living room was comfortable and great for relaxing or watching a film. The lower level playroom was great fun with ping pong and billiards set up in two areas. We found everything we needed including electric outlets where you need them. The location was great for us and our rides to Montauk and the other towns in the area for museums and restaurants and views. The only thing less than perfect was low water pressure in the master bath sinks and shower, which Abigail said the plumber was addressing. She was extremely responsive and helpful.

Weekly house rentals

Guest favourite
Home in Westbrook
4.96 out of 5 average rating, 26 reviews

Barnacle Bay Beach House

AshlynRating, 5 stars1 week ago
My husband, dog, and I LOVED our stay here- so much that Danielle accommodated for us to stay an additional day! It was the perfect location. Private enough where we felt secluded, but yet right off of a main road with so many great restaurants to walk to! The beach was about a 5 minute walk, and left us with the perfect spot and feeling like we had the beach completely to ourselves the days we were there. We are already talking about going back, and can’t wait to plan our next trip. Thanks so much!
Guest favourite
Home in Clinton
4.89 out of 5 average rating, 18 reviews

Boulder Lake House Retreat

AmandaRating, 5 stars6 days ago
Great stay! Although it was a rainy weekend, we had a great weekend!! There were close restaurants and coffee shops and the house itself was perfect. Great aesthetic to the home, very cozy and relaxing.
Top guest favourite
Home in East Marion
5 out of 5 average rating, 13 reviews

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV

SamanthaRating, 5 stars1 month ago
Can not recommend more! Beautiful house and perfect location! Would love to come back. Kids loved the beach and finding shells and little sea creatures in low tide!
Guest favourite
Home in Old Saybrook
4.72 out of 5 average rating, 224 reviews

The Cottage

KatieRating, 5 stars2 weeks ago
This was the perfect place to stay for our weekend get away. It’s a great location close to a lot of restaurants, shopping, and beaches. We had everything we needed and the beds were very comfortable. We would definitely stay there again.
Guest favourite
Home in East Lyme
4.93 out of 5 average rating, 30 reviews

Stylish Retreat Waterviews

EmilyRating, 5 stars3 days ago
Our stay was perfect! Relaxing and inviting.
Superhost
Home in Essex
5 out of 5 average rating, 4 reviews

Mid-Century 4 bedrooms with Water View & Access

PriyaRating, 5 stars2 weeks ago
We had a wonderful weekend at Aude's home in Essex. The setting was beautiful and the house itself was immaculate. It is a 7 minute drive to the center of town, which was convenient. The host was very responsive and quick to fix any concerns we brought to her attention. I would definitely return to this Airbnb!
Guest favourite
Home in East Haddam
4.88 out of 5 average rating, 48 reviews

Historic House by the River

DhaniRating, 5 stars1 month ago
This house and host exceeded all expectations. House was historic facing the CT River & Goodspeed Opera House. Great sunsets. House is clean and well appointed with comfortable beds and bathroom facilities. Kitchen is spacious and eating areas comfortable. Andrea is extremely responsive and accommodating. Will be back again.
Top guest favourite
Home in Guilford
5 out of 5 average rating, 61 reviews

Field of Dreams Hot Tub - Fire Pit Retreat

JoshuaRating, 5 stars3 weeks ago
Field of Dreams is a beautiful, spacious, well-appointed home. Brenda is an attentive, gracious, and thoughtful host. My family and I stayed there for four stellar days over Memorial Day for my daughter’s college graduation. We hosted a big family dinner with a private chef that was excellent. And Brenda really helped us with some of the details. This is a lovely home and I highly recommend it.

Private house rentals

Guest favourite
Home in East Hampton
4.95 out of 5 average rating, 65 reviews

Country getaway - pool, huge yard,

TressiaRating, 5 stars3 weeks ago
Lena was wonderful. She warmly welcomed me and my guest, making our stay very comfortable and easy. She even left me a note with birthday wishes, along with a box of delicious baked cookies. The apartment is charming and spacious, located on top of their home, with a large yard and peaceful scenery.
Guest favourite
Home in Old Saybrook
5 out of 5 average rating, 40 reviews

Romantic Couples Retreat with Private Sandy Beach

RajRating, 5 stars3 weeks ago
Fantastic cute spot in Old Saybrook. Key things for future guests to know - there is no A/C in the winter months so the air can get a bit stale / stuffy in the house. Plus there is no washing machine / dryer in the house, so defo bring enough clothes!
Top guest favourite
Home in Madison
5 out of 5 average rating, 28 reviews

Stylish Modern Home, 4-Bedroom, Madison CT

AlanRating, 5 stars3 months ago
Sascha was a terrific host and we had a wonderful stay at his home. The home was beautiful: plenty of space to spread out, relax, and everything was incredibly clean and tidy. It was also well-stocked with everything you could need. We appreciated Sascha's friendly demeanor, and he was a pleasure to communicate with. We hope to return here in the near future for another stay.
Guest favourite
Home in East Hampton
4.89 out of 5 average rating, 27 reviews

Lakeside Paradise with Breathtaking Sunsets

KariRating, 5 stars2 weeks ago
Joshua’s place was beautiful, literally right on the lake. Unfortunately, we got rained out as we were looking forward to kayaking out to the 2 islands. We had plenty of space to lounge, read, and watch TV. Joshua responded quickly whe we had a question. It was a wonderful weekend!
Guest favourite
Home in Haddam
4.98 out of 5 average rating, 80 reviews

Winter at the Haddam House

MaryRating, 5 stars3 weeks ago
I can't say enough good things about John and Betsey's beautiful little river cottage. We traveled to Connecticut from Oregon for our daughter's college graduation and the cottage ended up being the perfect place to stay. It was an easy, traffic-free twenty-minute drive from the college (Wesleyan) and allowed us to retreat each day from the fray and intensity of graduation move-out activities. The setting is fantastic--peaceful, right on the river, with a lovely seating area right at the river's edge, with incredible views of the East Haddam Swing Bridge, the historic opera house and inn across the way, and just enough river activity to keep things interesting without ever being loud or intrusive (we were there in late May). The house itself is very comfortable, with a lovely view of the river from the living room, a well-stocked kitchen, and really anything you could want or need (including lots of games). The house is also walkable or a short drive to coffee, shops, and groceries.
Top guest favourite
Home in Madison
5 out of 5 average rating, 37 reviews

Waterfront Beach House with pool

Andrew & HeatherRating, 5 stars1 week ago
Meaghan was a wonderful host who was very prompt, kind, and respectful of privacy. The house itself was stylish, comfortable, and modern while being kid friendly which is a tough thing to achieve in any home let alone an Airbnb. The view from the house was an absolute highlight! We had a great time!
Top guest favourite
Home in Old Saybrook
5 out of 5 average rating, 53 reviews

Great Hammock Getaway | Beaches, Views & Hot Tub

Carl And AnneRating, 5 stars5 days ago
This was our second stay at this lovely home. It was the perfect place to spend a week celebrating our 51st anniversary! The house itself is beautifully decorated, impeccably clean, and offers everything we could need for cooking, comfort, and leisure. We especially enjoyed the gas fireplace and the hot tub! We made good use of the local beach pass that was furnished for us. The two very close by beaches were well-maintained and very enjoyable. We would highly recommend this location and plan to make this our go to Airbnb when we are in this area. Irina is the perfect host! She is extremely responsive and reliable.
Top guest favourite
Home in Old Saybrook
5 out of 5 average rating, 47 reviews

3BR Updated Cottage w/ Pool in Old Saybrook

BrianRating, 5 stars2 weeks ago
This house was perfect for our long weekend getaway. Everything was as described and absolutely spotless - including the pool. I would highly recommend Julia’s house for both short and long stays as there is plenty to do and see in the area and the house is close to everything yet tucked away for peace and quiet and beautiful views.

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