Photo by Darrell Bumbala

Holiday Homes in Stratford

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Featured Holiday Homes in Stratford

Business or Weekend escape

9.6 out of 10, Exceptional, (30)
"Stayed for my other half bday. Place was clean and described well"
The price is AU$154
includes taxes & fees
2 Dec - 3 Dec
Business or Weekend escape

Family Gem on Dyer Street

10.0 out of 10, Exceptional, (2)
"Needed a place to stay for the night and it was just the perfect spot. The house was just as it seemed online and it was a lot bigger than I expected. Everything was really nice and the host was super nice and very easy to communicate with. Would 100% recommend to others for their next stay."
Family Gem on Dyer Street

3BR Paradise in Port Jefferson!

3BR Paradise in Port Jefferson!

Soundview Beach House: 4BR,Panoramic Views 1.5hrsNYC, Sits Directly on beach

9.8 out of 10, Exceptional, (64)
"The house was exactly as advertised, the water views were beautiful! Easy access to the North Fork of Long Island."
Soundview Beach House: 4BR,Panoramic Views 1.5hrsNYC, Sits Directly on beach

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (23)
"Washer downstairs unavailable, thermostat only on request, feather pillows (allergy). Otherwise it was ok with plenty of bedrooms and baths. "
Cheerful 4 bedrooms residential house.

Cozy 4-bedroom house with AC and WiFi in Centereach, New York.

10.0 out of 10, Exceptional, (22)
"Nice place—modernized and spacious! Perfect for families/friends weekend with separate basement suite! "
Cozy 4-bedroom house with AC and WiFi in Centereach, New York.

Waterfront Beach House w/ Water Views on The North Shore Long Island. 4 BRs 2BRs

9.6 out of 10, Exceptional, (99)
"Perfect location for nearby wedding (Old Field Club in East Setauket) and for places to shop and explore. Beautiful view , comfortable for the 6 of us. Would stay there again."
Waterfront Beach House w/ Water Views on The North Shore Long Island. 4 BRs 2BRs

Bright Milford Beach House w/ Outdoor Shower

10.0 out of 10, Exceptional, (5)
"Cute place right across from the beach. Had everything that you need to cook, even a vegetable garden with fresh tomatoes. Comfortable and clean. The beach access is across the street,. "
Bright Milford Beach House w/ Outdoor Shower

Coastal Bungalow Sanctuary, Game Room, Ocean Views

8.8 out of 10, Excellent, (11)
"The house was clean and the just was very nice‼️"
The price is AU$619
includes taxes & fees
2 Dec - 3 Dec
Coastal Bungalow Sanctuary, Game Room, Ocean Views

Home on the sound

8.6 out of 10, Excellent, (7)
"This was a greay stay and the property was really cute and cozy. It is an upstairs portion of a duplex "
Home on the sound

Walkable New Haven Retreat w/ Ocean Views!

9.6 out of 10, Exceptional, (21)
"We had a great time. Location was perfect and the staff was super responsive and flexible."
Walkable New Haven Retreat w/ Ocean Views!

Ranch style living at its best with country garden & patio!

9.8 out of 10, Exceptional, (7)
"We had a great time at this home and it is really fabulously decorated. Reggie called us right back when we had a question. "
Ranch style living at its best with country garden & patio!

Near Yale 8 beds Gaming Room

The price is AU$1,707
includes taxes & fees
1 Dec - 2 Dec
Near Yale 8 beds Gaming Room

Sunny East Haven Home w/ Grill: Walk to Beaches!

2.0 star property
10.0 out of 10, Exceptional, (3)
"6 of us stayed here for a music festival. The location, fantastic! Ocean views, check. The bedding, the furniture, kitchen supplies....no amenity was overlooked. Happened to meet owner when were checking in. He was great. Couldn't have been more accomodating. Great great place for a few nights or longer. Wush we were here longer. "
Sunny East Haven Home w/ Grill: Walk to Beaches!

Waterfront 3-bedroom house with AC and WiFi in tranquil Southbury

8.0 out of 10, Very good, (2)
"My husband, daughter and myself stayed at the house for a couple nights. The house was spacious, clean, had comfortable beds and was right on the lake. We loved that! Unfortunately, we arrived in the dark and the roads were a little tricky at night for our first time driving it. I know by the picture that there were some stairs to get to the house. I was thinking maybe 20 but 75? Since my husband has knee issues and I have back issues, it would have been good information to have on the...
Waterfront 3-bedroom house with AC and WiFi in tranquil Southbury

BREATHTAKING BUNGALOW-HOME AWAY FROM HOME

10.0 out of 10, Exceptional, (25)
"The house was clean, and very comfortable. They are well stocked, even with our odd allergies, we were able to find some snacks. It saved us a good amount of town since it was a short visit. "
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME

Gorgeous Victorian direct ocean front single family six bedroom, ten rooms

10.0 out of 10, Exceptional, (58)
"Great"
Gorgeous Victorian direct ocean front single family six bedroom, ten rooms

Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center

9.8 out of 10, Exceptional, (17)
"This place was super clean and exactly as described. "
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center

Beautiful 4BR Beach House with Private Beach Access.

9.8 out of 10, Exceptional, (69)
"our annual girls (5) trip took us to Branford, CT this year. It was awesome to have a private beach access even though we couldn’t get in the water, but it was great for strolls and shell collecting. Would definitely do better with a second bathroom, but we managed just fine. Overall, it’s a nice little place to stay for a getaway. My only issue is not with the hosts or place, but with one of the fees and the checkout process. However, it does not take away from our stay. "
Beautiful 4BR Beach House with Private Beach Access.

Stay 3 Nights or Longer Until January 31 and Get 15% Off

9.8 out of 10, Exceptional, (28)
"Property and home are beautiful. The larger home on adjacent property (Sunny Day) is close and if a larger group is staying there can be loud in the tranquil setting during the day. Otherwise, the setting is beautiful and the house was perfect for our family of 6 (3 couples). We enjoyed the kayak, paddle board, fishing, evening fire pit and views from upstairs deck and downstairs patio. "
Stay 3 Nights or Longer Until January 31 and Get 15% Off
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Stratford

Business or Weekend escape

9.6 out of 10, Exceptional, (30)
"Stayed for my other half bday. Place was clean and described well"
The price is AU$154
includes taxes & fees
2 Dec - 3 Dec
Business or Weekend escape

New Haven Village Suites

3.0 star property
7.6 out of 10, Good, (1966)
"Convenient location, helpful staff, comfortable bed. Thanks!"
The price is AU$175
includes taxes & fees
10 Dec - 11 Dec
New Haven Village Suites

Beachfront Romance: Rustic Home w/ Private Beach

9.2 out of 10, Wonderful, (46)
"We were looking for a small and private beach house getaway for the weekend and found this hidden gem. Our property manager, Debbie, made herself available throughout our stay to answer all of our questions. Everything needed for our comfort weekend was provided. We strongly recommend this place for those who are looking to get away from the hustle and bustle of city life. We will be returning! "
Beachfront Romance: Rustic Home w/ Private Beach
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.