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House holiday rentals in Guilford

Find and book unique houses on Airbnb

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Popular amenities for Guilford 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!!
Superhost
Home in East Hampton
4.88 out of 5 average rating, 111 reviews

Modern East Hampton Home w/ Heated Saltwater Pool

MariaRating, 5 stars4 weeks 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.
Top Guest favourite
Home in Monroe
4.97 out of 5 average rating, 201 reviews

Garden Level Suite with Beautiful Pool

GraceRating, 5 stars3 months ago
We had an amazing time at Marybeth’s suite—it truly felt like a winter wonderland. Our kids had a blast "swimming" in the snow and "rolling" over the gentle hills. Every moment was filled with joy, whether we were relaxing in the sunroom, playing in the snow, or swinging outside. The time spent together as a family, along with our conversations with Marybeth and her family, was truly precious. We can’t wait to return in the summer!
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 North Fork
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 East Hampton
4.93 out of 5 average rating, 154 reviews

Large heated pool, games room, near private beach

BerniceRating, 5 stars4 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.
Guest favourite
Home in Montville
4.95 out of 5 average rating, 151 reviews

Casino Stay & Play House

NurisRating, 5 stars2 weeks ago
I loved spending my birthday with my family. It was the perfect place for my family. Everything was so clean and organized. I am very grateful for everything. Thank you

Weekly house rentals

Superhost
Home in North Branford
4.9 out of 5 average rating, 10 reviews

The Gait House at High Gait Farm

NancyRating, 5 stars2 weeks ago
Lori was very accommodating to us with early check in. The beds were super comfortable, and I was so happy to see that she had two king sized beds and one queen! Perfect for our family. Beautiful linens, tons of comfy white towels in the bathrooms. Really a great place to stay that I would highly recommend.
Superhost
Home in Guilford
4.88 out of 5 average rating, 51 reviews

The Davis House

PhilipRating, 5 stars3 weeks ago
we have stayed at this place multiple times. It is very conveniently located near our kids and also very easy to get to. It is spacious and comfortable and clean. The house is a bit on the “vintage” side, but that shouldn’t matter, and it contains pretty much everything you could want as a guest in a house. It is a little on the pricy side, but if you need three bedrooms and three bathrooms, it is a good value. And Sharon is very responsive. She does have particular rules and expectations, but nothing more than should be expected of a good guest in someone’s house. (as opposed to being a hotel guest where you don’t need to clean up after yourself) we strongly recommend this place.
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.
Top Guest favourite
Home in North Fork
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 East Haven
4.95 out of 5 average rating, 40 reviews

Direct Beachfront Modern Cottage on Private Beach

MacKenzieRating, 5 stars3 weeks ago
We had a great stay at the Airbnb. One thing I haven’t seen mentioned in the reviews or descriptions is that this beach had tons of sea glass! In our short stay we found over 100 pieces and my 4 year old was absolutely delighted scouring the beach for it. There are also tide pools less than a five minute walk from the house. These two things made the stay quite magical for my kids. Otherwise the location is great and the house was very clean. I appreciated the bed on the first level having a trundle as well as a door at the top of the stairs for safety. The house is minimally decorated which is honestly a plus when you don’t have to worry about your kid breaking nicknacks on coffee tables. A few nice throw blankets and nicer glassware would have added to the stay though. Overall we were very happy with this property.
Guest favourite
Home in Haddam
4.97 out of 5 average rating, 29 reviews

The Farmhouse Stay

MarisaRating, 5 stars3 weeks ago
Chelsea was communicative and helpful about her beautiful house. It had all we needed, was well appointed, beautifully decorated and in a gorgeous natural setting. We spent time lounging in the living room as a family and it was so comfortable. Top notch! Grab this place now!
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!
Guest favourite
Home in Clinton
4.84 out of 5 average rating, 57 reviews

Summer by the Beach,Outlets,Golf at the GlassHouse

MarissaRating, 5 stars1 week ago
This home was very spacious and clean. It was great to have the pool table, foosball and air hockey tables. This house had everything we needed and was only a 5-10 minute drive from restaurants, shopping and beaches. Great location!

Private house rentals

Guest favourite
Home in Branford
4.83 out of 5 average rating, 54 reviews

King Suite with Private Bath and Private Entrance

PaulaRating, 5 stars1 month ago
Great location, just down the street from the beach! Branford was a short drive, great shops and restaurants.
Guest favourite
Home in Branford
5 out of 5 average rating, 54 reviews

Beach House in Private Community on LI Sound

ColetteRating, 5 stars1 day ago
Bill's Branford home is beautiful and very comfortable. We enjoyed the back porch, the clean and modern kitchen, the two living rooms, and all of the unique artwork Bill's family has collected over the years. Our two year old loved all the toys and books in his room! The house was perfect for our family gathering. Not to mention the amazing location just steps from the beach. We definitely recommend it. Thank you, Bill!
Guest favourite
Home in West Haven
4.96 out of 5 average rating, 45 reviews

Westshore Luxury

MatthewRating, 5 stars1 week ago
You, was great. Traveling through and not knowing much about the area. Yu gave us so much helpful information. Be sure to ask Yu about their great restaurant in New Haven.
Top Guest favourite
Home in Branford
4.98 out of 5 average rating, 40 reviews

The Eagle- Private Beach

StephanieRating, 5 stars3 weeks ago
Great location with private beach access. Cozy 2-bedroom slept our family of 4 comfortably. Comfortable beds, great shower pressure, and large yard out back. I’m originally from Branford and we visit my parents regularly. Will definitely keep Abigail’s home in mind for future visits!
Top Guest favourite
Home in Haddam
5 out of 5 average rating, 23 reviews

The Doll House

EthlynRating, 5 stars1 week ago
Jeremy’s “Doll House” was a charming little place on lovely peaceful grounds. The location was very convenient for visiting our Connecticut relatives and attending our granddaughter’s graduation. His kitchen is well stocked with all the essentials and then some. Everything was very clean and the bed was very comfortable. There is a huge walk in closet in the bedroom and great laundry area in the bathroom. I would recommend Jeremy’s place and would stay there again.
Guest favourite
Home in Guilford
4.96 out of 5 average rating, 24 reviews

The Osprey Nest w/views of Long Island Sound

AlexRating, 5 stars5 months ago
This is a great place! I just finished my fourth visit (approaching 50 nights in this home) and I didn’t want to leave. Book this place if you want to wake up and drink coffee while watching sunrise in a second floor sun room or if you want a 1 mile walk to town (all sidewalks) and 200 meter walk to beach or if you want a place that’s stocked with kitchen utensils! I could go on and on. If it matters, it’s also not a corporate type Airbnb. Recommended!
Guest favourite
Home in North Fork
5 out of 5 average rating, 17 reviews

Hang by the (Chel)SEA

JillRating, 5 stars2 weeks ago
Spent to my birthday here with my husband, dogs and toddler. Had my gender reveal birthday cake, outback under the sunset. Truly magical.✨ The backyard was ideal. Was able to tie the dogs to the deck with a 20 foot leash. It kept them contained to the backyard & away from beach goers on foot and other dogs. The dunes kept the backyard private you’re not staring at your neighbors. Felt so secluded. I also have some mobility issues and you couldn’t ask for an easier way to enjoy the beach & get your toes in the sand. The house & deck are spacious and easy to navigate with a walker. Was able to add extra days to our stay. Would 100% stay here again.
Guest favourite
Home in East Hampton
5 out of 5 average rating, 19 reviews

CT River Retreat - Modern Home with CT River Views

BrianaRating, 5 stars2 weeks ago
We had an amazing stay at Peter’s home by Saint Clement’s Castle for our wedding weekend! From start to finish, Peter was an exceptional host—friendly, responsive, and incredibly flexible with the details of our stay, which helped make a busy and emotional weekend so much smoother. The home itself was spotless, modern, and thoughtfully maintained. Every room felt comfortable and inviting, and the clean, updated aesthetic made it the perfect place to relax between events and get ready for our big day. It truly felt like a peaceful retreat during a very special time in our lives. We couldn’t have asked for a better experience and would absolutely recommend Peter’s place to anyone visiting the area—especially for events at Saint Clement’s. Thank you again, Peter!

Quick stats about house rentals in Guilford

  • Total rentals

    60 properties

  • Total number of reviews

    2.8K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    60 properties include access to Wi-Fi

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