House holiday rentals in Middlesex County

Find and book unique houses on Airbnb

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Popular amenities for Middlesex County house rentals

House rentals with a pool

Superhost
Home in Hampton Bays
4.79 out of 5 average rating, 103 reviews

Private completely fenced in property. Near beach.

KarenRating, 5 stars2 weeks ago
This is a beautifully furnished large home with lots of extras, including very well outfitted gym, hot tub and pool (although the pool was not open yet during our visit). The backyard is huge and our dogs loved it. All of the bedroom are spacious and well appointed. It is a great entertaining house or a family with kids. We loved and in fact have already re-booked it for another visit!
Guest favourite
Home in East Hampton
4.88 out of 5 average rating, 106 reviews

4 BD w/ Heated Pool in E Hampton, Fully Furnished

IanRating, 5 stars2 days ago
We had a wonderful time in this beautiful home that is in an idyllic Hampton's setting. Ashton was a great host and for sure we will be back.
Top Guest favourite
Home in Cheshire
5 out of 5 average rating, 131 reviews

Pool House

MelissaRating, 5 stars3 months ago
This was our second time back to the pool house and it was amazing, again. We thinks of everything to make you feel welcome. Milk and eggs in the fridge. Muffins and croissants waiting for you. Pristine home. Fully stocked kitchen. I was even able to host a few family members for Christmas dinner and had everything I needed to make a lovely dinner. We also travel with two dogs and Sue is so accommodating, making our pups feel right at home. Thank you, Sue, for making our holidays away from home so peaceful and enjoyable.
Top Guest favourite
Home in East Hampton
5 out of 5 average rating, 36 reviews

Stunning Central E. Hampton Home w/ gunite pool.

DonnaRating, 5 stars3 months ago
Our family enjoyed a wonderful post- Christmas getaway at Jennifer’s beautiful home. The house is fabulous - well- located, pristine , beautifully decorated and well-stocked. It was relaxing and perfect. We did not have much need to reach out (everything was effortless) but when we did, Jennifer was very responsive and helpful. Highly recommend!
Guest favourite
Home in East Hampton
5 out of 5 average rating, 5 reviews

The Hideaway

NikkiRating, 5 stars7 months ago
Dorina’s home was the calm, peaceful reprieve from the city we were looking for. Her home was so comfortable and she went above and beyond to make sure we had everything we needed. The backyard was a little oasis with a large pool (with floats!), several (6 I think) lounger chairs, two 6 top tables in different areas and a functioning grill. We spent most of our time here! Dorina was fast to respond, helpful with recommendations and overall what you hope to have in a host. We would definitely come back to Dorina’s home!
Top Guest favourite
Home in East Marion
5 out of 5 average rating, 11 reviews

Long Island home w/ large pool

LoreleiRating, 5 stars4 months ago
This house was fantastic! We cooked a full Thanksgiving dinner here! The house was well stocked with everything we needed, from kitchen essentials to paper products. The layout of the house was great. Jane was very accommodating and made things easy for us! The house was immaculate and met all of our needs. I hope it’s available next Thanksgiving! Perfect location! Close to town, yet quiet and private! It was my granddaughter’s first Thanksgiving and I’m so glad we had this house to celebrate in!
Superhost
Home in East Hampton
4.94 out of 5 average rating, 16 reviews

Walk to Water. Stunning Home with Gorgeous Pool & Grounds.

LarryRating, 5 stars46 months ago
House is well represented. Spacious, very clean, and great location. Good for families or groups of friends.
Guest favourite
Home in Southampton
4.96 out of 5 average rating, 165 reviews

POOL in APRIL! Waterview, Free For Dogs! Kayaks

JackRating, 5 stars3 weeks ago
The stay was fantastic, we wanted a quick getaway for the weekend, and their home was the perfect spot. We enjoyed the space by the fire and the cleanliness of the spaces. We would love to come back for a longer stay.

Weekly house rentals

Guest favourite
Home in East Hampton
4.95 out of 5 average rating, 60 reviews

Country getaway - huge yard, pool

KetwlyRating, 5 stars5 months ago
Our stay was wonderful. Lena is the perfect host. We are already talking about going back next fall!
Top Guest favourite
Home in Old Lyme
4.94 out of 5 average rating, 268 reviews

Modern Luxurious CT Country Home

AnirudhyaRating, 5 stars1 month ago
Chris was a fantastic host! First of all he was so responsive, always checking in on us everyday, and very helpful and communicative with recommendations and quick answers. Second of all, the property. It is so gorgeous. Definitely worth the price, and maybe even better! We loved our stay, we will definitely be coming back soon. Definitely check it out if you’re considering an Airbnb in the area. 10/10 experience!
Superhost
Home in Westbrook
4.85 out of 5 average rating, 190 reviews

Family-Friendly Cottage by The Shore

AbdouRating, 5 stars1 month ago
Westbrook is a beautiful area. Bill’s seafood was amazing and it was minutes from the house. We went in early March, and still the local beach was a joy. It was a perfect weekend getaway for us.
Guest favourite
Home in Middletown
4.88 out of 5 average rating, 299 reviews

Historic Greek Revival Brick Home

JamieRating, 5 stars1 month ago
If you like antiques and a classic style home, Bill and Megan's place is for you. The woodwork and fireplaces were beautiful, and the space itself was simply charming. Check in directions were very easy to understand and we appreciated the off-street parking. The property was within easy walking distance to many shops and restaurants. We would definitely stay at this residence any time we visit Middletown.
Top Guest favourite
Home in Madison
5 out of 5 average rating, 28 reviews

Stylish Modern Home, 4-Bedroom, Madison CT

AlanRating, 5 stars1 month 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 Middletown
4.95 out of 5 average rating, 40 reviews

Hot Tub and pool Home away from home

KristenRating, 5 stars3 months ago
Jan's house was a great stay with plenty of room for six adults. We loved the game room and outdoor hot tub. Instructions for the hot tub were clear and easy to follow. We'd definitely stay again!
Guest favourite
Home in Madison
4.87 out of 5 average rating, 23 reviews

Historic Beachside Glamour

GretchenRating, 5 stars5 months ago
A lovely cottage on a quiet street (at least in the fall!). The interior is just beautiful with all the wood floors, walls, ceilings. The kitchen was - unusual! Clearly they had to retrofit an old home to accommodate modern appliances, but all worked well.
Superhost
Home in Westbrook
5 out of 5 average rating, 3 reviews

Sunset Skies 2nd Fl | redone+walk to Water’s Edge

CarrieRating, 5 stars5 months ago
Great stay! One of the best AirBnB accomodations we have visited; everything was perfect! The location is ideal to walk to Water's Edge Resort or downtown Westbrook, very close to the beach. The stay was beautiful with brand new amenities, exactly as described. Kelly was very responsive, kind and helpful with any questions we had. We cannot wait to stay here again for a future stay.

Private house rentals

Top Guest favourite
Home in Old Lyme
4.98 out of 5 average rating, 55 reviews

Relax & Rejuvenate in this 1920s Riverfront Estate

JasonRating, 5 stars5 months ago
My family and I have rented several homes for vacation over the years, but this home is truly a special place. The property is gorgeous! The views are amazing, and we enjoyed spending many hours taking it all in. Lots of wildlife to observe and the private hiking trail was a great bonus. The house itself was wonderful…a unique mix of history, art, music, and modern technology. Everything was high-end and excellent quality. The bed in the master bedroom was the most comfortable we have ever slept in away from home. The house was extremely clean and had everything you would ever need and plenty of it. We have never seen a vacation house with so many extra linens, toilet paper, Kleenex, coffee, etc. We were so impressed! Hector is an exceptional host, friendly and responsive. His home is incredibly peaceful, a true sanctuary. We are so very grateful that we chose this house for our family vacation. Thank you, Hector!
Superhost
Home in Guilford
4.88 out of 5 average rating, 49 reviews

The Davis House

WilliamRating, 5 stars3 months ago
Would absolutely book again. We were travelling as a family of four (teenager and an elementary schooler) to visit family in Guilford area. This was a great space for us, three bedrooms and baths, den, sitting room, kitchen, dining area. You could do this as a family of five pretty easily, maybe six if someone sleeps on a couch. There's a back porch we didn't use due to cold weather but I suspect is lovely in summer. The residence is well maintained and tastefully decorated, I suspect some of the wall decorations are at Sharon's store. Wi-fi and TV with tubi subscription, and there were some board games in the closet. Sharon noticed snow in the forecast and salted the driveway and walk before we arrived. We didn't experience any problems per se but Sharon was very responsive when we had questions. We had a really positive experience.
Guest favourite
Home in Clinton
4.96 out of 5 average rating, 25 reviews

Zaku’s Lake House

KathleenRating, 5 stars7 months ago
We had a wonderful stay! This is our second time staying in the home and both times Mariza was accommodating and great to work with. The house is in a great location on the water and is clean and maintained very well. We plan to stay again in the future!
Top Guest favourite
Home in Guilford
5 out of 5 average rating, 18 reviews

Coast and Country Private Estate

AlisonRating, 5 stars5 months ago
We stayed at this property the weekend of our daughter's wedding. Susanne was an absolute gem of a host. She checked in the day of our arrival and departure. The house was beautiful, the property and grounds are secluded, quiet and surrounded by nature. Often times a rental feels just like that, a rental. This, however, was as if we'd been invited to spend the weekend at a good friend's home. I would highly recommend this location.
Superhost
Home in Essex
4.95 out of 5 average rating, 19 reviews

Hyde House-A classic New England cape.

SofiaRating, 5 stars3 months ago
Fred’s house was beautiful! Felt home from the moment we walked in. It was clean and cozy! We enjoyed walking to Essex Village (which is so beautiful and charming) it is a very peaceful place and people around are very kind
Superhost
Home in Old Saybrook
5 out of 5 average rating, 3 reviews

Fenwood Coastal Getaway Private Beach Access

MichelleRating, 5 stars7 months ago
Jasons house was a perfect, comfortable stay for our group attending a wedding. It is a block from the water and gives you access to the private beach. The beds and couch were very comfortable and the space was clean.
Guest favourite
Home in Clinton
4.82 out of 5 average rating, 49 reviews

Glass House-Beach 5mins/Outlets 5mins/Golf 5mins

LuzRating, 5 stars3 days ago
Beautiful house and peaceful area to relax and enjoy extra time with your loved ones, and fun family activities right inside the house! Everything you need for a relaxing stress free getaway! The owners are very nice friendly family, they but a lot of attention and dedication to house to make it feel and look like your right at home. Love, Love, Love!
Top Guest favourite
Home in Guilford
5 out of 5 average rating, 24 reviews

Entire home - Cheerful 4 bedroom on the shoreline.

AshleyRating, 5 stars5 months ago
Beautiful spacious house in an excellent location. Host greeted us upon arrival, which was extra, and appreciated. Very clean uncluttered house- clean linens and towels. Beautiful yard. Walkable neighborhood and proximity to beach and town is ideal. Totally recommend, and we would definitely rent this property again! Fresh dahlias in the kitchen!

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