
Family-friendly vacation rentals in Guilford
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Top-rated family-friendly rentals in Guilford
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
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Popular amenities for Guilford family-friendly rentals
Family-friendly home rentals with a hot tub

Luxury Penthouse Minutes to Yale
Great location. Easy check in and out.

ZoomIn Map BestTown Washington "Kirby" PoshPadsCT
Beautiful house, gorgeous and convenient location, excellent host. We had a great stay.

Villa Flora @ Norwich Inn & Spa
There is nothing more frustrating than not being able to have a decent shower while you are on vacation. That was absolutely not the case here. The hot water and water pressure in both bathrooms was exceptional. This is a great place in a great area. We will definitely try to get back here.

Private Oasis W/Stunning Vinyard and Pool Views
This is the 2nd Thanksgiving weekend we spent at Deeanna's. Her home is beautiful, comfortable and each detail is thought though in the best way. Deeanna went above and beyond to accommodate my family and we are so grateful to her. The kitchen is perfection and the bedrooms are lovely and comfortable. The scenery and views are breathtaking. Overall, this home is a total gem. Thank you, Deeanna! We hope to come back next year!

Family Friendly Springs Beach House
Fantastic stay/fantastic hosts! My adult children and I spent a great weekend hosted by David and Abby. Their place was perfect for us and very comfortable. David reached out and described check in and proactively answered any questions we would have had. We were there in cold weather but I will earmark it for a warm weather stay as it has so many appealing summer amenities! We will stay again for sure.

Newly Renovated w/ Pool, Hot tub & Fireplace
We had a wonderful stay at Jennifer’s place. It was.l beautiful, immaculate, and incredibly well equipped—especially for kids with the plethora of games and toys. Jennifer was responsive and a great host. The house is on a serene, dead-end street, and outdoor area is perfect for kids.

Captains Quarters | July avail!
This house served our family very well for a multi-month stay. The house and property are just like the photos and all the amenities were great to have. Would recommend staying here if you are looking for a quiet place near the water in East Hampton. Petra was always very responsive with anything we needed and was an excellent host.

Grand 9 BR Near Casinos
We loved staying here- it made for a perfect weekend. Thank you so much for welcoming us in your home!
Family- and pet-friendly home rentals

On the Park: 3 RM Apt. w/kit. in historic house
Noel was an incredibly gracious and friendly host, providing us with everything we needed for a great stay in her apartment. The apartment itself is so cozy; we particularly enjoyed the library room and exploring the hundreds of titles Noel keeps there. I would recommend Noel’s apartment to anyone that is making a trip to New Haven.

Lake Beseck cottage
Was the perfect little get away for us. And it was nice to find a place that accommodated the dogs so well. We appreciated being able to get to places easily but at the same time have a peaceful place to return to.

The Farmhouse Estate Apartment
This was the perfect place for our family to stay! There was plenty of space and everything we needed was provided. We would definitely stay here again!

Squire Chase House
Great spot! Very walkable. It's also a great layout if traveling with small children - there is a separate meditation room upstairs that was perfect for setting up our travel cribs. Would stay again!

House on Little River / Writer Retreat
Cabin on Little River met our expectations and more. Myself, 2 sisters and my daughter wanted a quiet getaway. A charming open concept post and beam, pine floors and wood trim, woodstove for winter, deck with charcoal grill. It's very rural and IN the woods ( so bring bug repellant). Even though the host's home is visible you still feel tucked away. Kitchen and bath are modern and clean and the beds and livingroom were very comfortable. The soothing sound of the river is always present. It was relaxing to sit down in the adirondack chairs near its bank. The woods provide a place to walk. Lake is across the road. Glenn informed us of several events nearby that we were really interested in...but we never felt like leaving the cabin! There's a big firepit nearby and wood provided. Glenn is a wonderful host. A fellow artist, I asked to see his studio on the ground level. Even bought a couple small paintings. Do not hesitate to book this place if you are looking for a quiet respite!

Unique apartment in former art gallery.
I really enjoyed my stay here. The place was eclectic and comfortable. I loved how open and spacious the home was and appreciated the peacefulness of the area. I would definitely stay here again on future visits.

3 bedroom near Wesleyan, downtown
Very nice place and location is amazing. We were grateful that our host provide some basic amenities - coffee, shampoo and condtuoner, etc. Made our visit easy and very pleasant. Thank you!

Private 1 bedroom apartment in central Connecticut
I chose Marlene’s lovely spot primarily because it was in a location convenient for short trips to visit family and friends in Wallingford, Middlebury and Middletown while on my way south from New Hampshire. The peaceful, quiet surroundings along with a spotless, well-appointed accommodation made it very appealing: highly recommended.
Family-friendly home rentals with a pool

Casino Wine Down House
House was very easy to get to and very clean. Surrounding neighborhood was nice and quiet. Outside igloo was warm and cozy. Downstairs game room was a hit with the big kids.

Sunset Oasis 1 @ Ocean Beach: $1Mil View 6 Queen
Great spot, would definitely stay again.

Escape to a Restored New England Antique Milk Barn
We had an amazing stay at Sally’s place in Bethel! My fiancé and I visited CT for the first time to celebrate my birthday and go to a convention nearby. This cottage was perfect for the two of us. The host was very responsive and accommodating as well! The cottage was in pristine condition, the house manual was very easy to follow, the recommendations were great, the scenery was out of a movie, and my favorite part was the hot tub in our restroom which was perfect after a long day! We had a great time and would love to come back again! Thanks for your hospitality Sally! ☺️

The Perfect North Fork Escape
We had a wonderful stay. Cute and comfortable house in an amazing location. Very comfortable for a family of 4.

Pool House
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.

Modern East Hampton Home w/ Heated Saltwater Pool
The house is beautiful, looks like photos. Stephen is a great host! Overall great stay, could not recommend more!

Garden Level Suite with Beautiful Pool
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!

Quiet, Upscale Retreat by the Beach with Pool
We had a lovely stay at Eric's home. The home exceeded our expectations and we felt right at home. The decor was warm and inviting. Everything you could possibly need was in the stunning, modern kitchen. The beds were all comfortable and we slept very well. The property was very peaceful. We enjoyed seeing deer, turkeys and hawks each day. The fixtures in the home were modern, clean and high-end. It was great being so close to Greenport with it's wonderful restaurants and shops. We can't wait to return.
Quick stats about vacation rentals that are family-friendly in Guilford
Total rentals
60 properties
Nightly prices starting at
$100 before taxes and fees
Total number of reviews
2.9K reviews
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wifi availability
60 properties include access to wifi
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- Beach
- Yale University
- Foxwoods Resort Casino
- Ocean Beach Park
- Cooper's Beach, Southampton
- Quotonset Beach
- Giants Neck Beach
- Shinnecock Hills Golf Club
- Woodmont Beach
- Clinton Town Beach
- Walnut Public Beach
- TPC River Highlands
- Amagansett Beach
- Thunder Ridge Ski Area
- Marvin Beach
- Jennings Beach
- Seaside Beach
- Shennecossett Beach
- Connetquot River State Park Preserve
- Long Island Aquarium
- Attawan Beach
- Groton Long Point Main Beach
- Bushnell Park
- Sunken Meadow State Park
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