Photo by Darrell Bumbala

Stratford Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Stratford Vacation Homes

Cozy 2 bedroom home located minutes from downtown
Interior

Cozy 2 bedroom home located minutes from downtown

9.6 out of 10, Exceptional, (29)
"Perfect stay for the Yale-Harvard game. "
Cozy 2 bedroom home located minutes from downtown
Stareway to Heaven Su
Terrace/patio

Stareway to Heaven Su

10.0 out of 10, Exceptional, (6)
Stareway to Heaven Su
Beautiful historic home in Stony Brook!
Interior

Beautiful historic home in Stony Brook!

2.0 star property
8.2 out of 10, Very good, (12)
"Thank you Great Location Would book again"
Beautiful historic home in Stony Brook!
Cozy 3 bedroom minutes from Yale and the beach
Private kitchen

Cozy 3 bedroom minutes from Yale and the beach

7.0 out of 10, Good, (2)
"The inside was very clean, the back patio/garden area is cute, but the pool was green by day two. Overall we enjoyed our time here"
Cozy 3 bedroom minutes from Yale and the beach
Amazing Rocky Point Retreat Overlooking the Sound!
Game room

Amazing Rocky Point Retreat Overlooking the Sound!

9.8 out of 10, Exceptional, (73)
"Love staying at this comfortable house each year for Thanksgiving and the location is perfect! "
Amazing Rocky Point Retreat Overlooking the Sound!
Charming 3-bedroom house with WiFi, AC in serene Fairfield
Fridge, microwave, oven, stovetop

Charming 3-bedroom house with WiFi, AC in serene Fairfield

9.6 out of 10, Exceptional, (4)
"Thank you for the stay!"
Charming 3-bedroom house with WiFi, AC in serene Fairfield
Business or Weekend escape
Pool

Business or Weekend escape

9.2 out of 10, Wonderful, (44)
"Very nice owner with great communication. "
The price is CA $117
CA $201 total
includes taxes & fees
Aug 13 - Aug 14
Business or Weekend escape
Cozy 4-bedroom house with AC and WiFi in Centereach, New York.
Private kitchen

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

10.0 out of 10, Exceptional, (34)
"Great place. Total of 7 of us travelled. Will absolutely use this property again. Thank you for everything!"
Cozy 4-bedroom house with AC and WiFi in Centereach, New York.
Minutes to Walnut Beach, newly renovated 3 bedroom home
Sun loungers, beach towels

Minutes to Walnut Beach, newly renovated 3 bedroom home

10.0 out of 10, Exceptional, (6)
"Very nice place."
Minutes to Walnut Beach, newly renovated 3 bedroom home
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
On the beach, sun loungers, beach towels

Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

10.0 out of 10, Exceptional, (121)
"Beautiful historic home, views of the Sound, pleasant walking neighborhood."
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
Stay at Black Rock Harbor
Exterior

Stay at Black Rock Harbor

10.0 out of 10, Exceptional, (21)
"Lovely home, responsive host & convenient location with water views. Cute & comfy decor with well appointed kitchen and off street parking. "
Stay at Black Rock Harbor
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC
Exterior

Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC

2.0 star property
10.0 out of 10, Exceptional, (5)
"We had a very nice family weekend. There was plenty of room, the furniture and beds were comfortable, and the kitchen had everything we needed. Great communication with the owner"
The price is CA $488
CA $957 total
includes taxes & fees
Sep 3 - Sep 4
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Outdoor pool, a heated pool

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

10.0 out of 10, Exceptional, (136)
"Perfect location for a get-away! Beautiful location on the water. The cottage was cozy & had everything we needed. Very clean. Lots to do in the area. Host was very nice We had a great time and will absolutely be back! "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Soothing Carriage House with Hot Tub in charming Stratford
Interior

Soothing Carriage House with Hot Tub in charming Stratford

10.0 out of 10, Exceptional, (1)
"John was a wonderful Host.We had a very relaxing time in the Hot Tub and the carriage house had everything we needed for our stay.We will definitely book again,Lisa and Holly"
Soothing Carriage House with Hot Tub in charming Stratford
Cheerful 4 bedrooms residential house.
Exterior

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (31)
"House was perfect for what we needed. Great proximity to the Amphitheater and Seaside Park. "
Cheerful 4 bedrooms residential house.
Gorgeous 4BR Beach House with Private Beach Access.
Beach nearby, beach towels

Gorgeous 4BR Beach House with Private Beach Access.

9.8 out of 10, Exceptional, (74)
"We loved our stay at this beautiful cottage. The entire experience was very smooth, from pre-check in to getting there and even offers to help with anything we needed in our stayThe cottage is very cozy and well-cared for. The rooms are comfortable and the Internet fast. There is a lot to do in the area, with New Haven nearby and many good restaurants."
Gorgeous 4BR Beach House with Private Beach Access.
Beach Bungalow, walk to beach, private backyard
Fridge, microwave, oven, dishwasher

Beach Bungalow, walk to beach, private backyard

10.0 out of 10, Exceptional, (3)
"The property was perfect for all of us. It was in a quiet neighborhood and great location."
Beach Bungalow, walk to beach, private backyard
Lakeside luxury: beautiful, relaxing 4 bedroom home
Property grounds

Lakeside luxury: beautiful, relaxing 4 bedroom home

10.0 out of 10, Exceptional, (27)
"This property was perfect for our needs! Checking in and out was simple and easy. The house is spacious and backyard is gorgeous! "
Lakeside luxury: beautiful, relaxing 4 bedroom home
Charming 2-bedroom house with WiFi, AC in Fairfield
Interior

Charming 2-bedroom house with WiFi, AC in Fairfield

8.0 out of 10, Very good, (3)
"Amalfi’s place was as described. It was clean and comfortable and mostly quiet. Amalfi was excellent with communication. Would certainly stay again when visiting family."
The price is CA $204
CA $474 total
includes taxes & fees
Aug 19 - Aug 20
Charming 2-bedroom house with WiFi, AC in Fairfield
Blue Cottage East Setauket
Fridge, microwave, oven, stovetop

Blue Cottage East Setauket

Blue Cottage East Setauket
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Stratford Hotel Reviews

The Circle Hotel Fairfield

The Circle Hotel Fairfield

10/10 Excellent
"This is my Go-To / First Choice when visiting the Fairfield area. Rooms are always clean & immaculate + very comfy bed, great towels, good size room...and traveling alone I feel safe! Staff is so welcoming and extra helpful. Keep it up."
Nancy 2-night trip
Posted 8 hours ago
The Circle Hotel Fairfield