Photo by Darrell Bumbala

Stratford Holiday Rentals

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Holiday Rentals 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
26 Nov - 27 Nov
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$174
includes taxes & fees
26 Nov - 27 Nov
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

DUNE Fairfield Beach

3.0 star property
8.8 out of 10, Excellent, (42)
"Beautiful and convenient location in a pretty neighborhood. Fairlt quiet on the 3rd floor, although some late night noise from party-ers but that was made clear on the website. Walkable to town and beach. Very comfortable stay! Thank you!"
The price is AU$446
includes taxes & fees
1 Dec - 2 Dec
DUNE Fairfield Beach

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

10.0 out of 10, Exceptional, (126)
"We stayed here for an anniversary weekend away and found the property and neighborhood to be amazing. We enjoyed the hot tub, pool and firepit and went kayaking in the afternoon. Enjoyed amazing sunsets from the deck; Adam gave us spot-on restaurant recommendations. I don't know if the supply of snacks is standard or an anniversary "special", but all in all this place was a wonderful find. Thank you!!"
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 star property
9.8 out of 10, Exceptional, (34)
"Great location! Clean building And modern. "
Luxury Furnished Apartments by Hyatus Downtown at Yale

Beach Apt. Wineries, Shopping, Dining

5.2 out of 10, (7)
"The property manager ensured that booking and check in went smoothly. If you're looking for a 5 star resort or party house, this is NOT the location for you. However, if you're looking for a peaceful getaway on the north shore of Long Island, within walking distance to the beach with your small family, including pet, check it out. Is it flawless? well, no. But you'll find flaws where you look for them. The better question in my mind would be "would I opt to stay there again?".. and the answer is...
The price is AU$419
includes taxes & fees
26 Nov - 27 Nov
Beach Apt. Wineries, Shopping, Dining

Luxury Designer 2 bedroom+office/3bed vacation home.

9.4 out of 10, Exceptional, (15)
"Great little spot. Central enough to get everywhere we needed to. Walked to restaurants and to a concert (about 30 minutes). Host had some treats for us when we checked in. Apartment was clean and spacious. Felt comfortable walking around the neighborhood "
The price is AU$651
includes taxes & fees
26 Nov - 27 Nov
Luxury Designer 2 bedroom+office/3bed vacation home.

Westport Paradise With Every Amenity!

10.0 out of 10, Exceptional, (23)
"We had such a nice stay at Mark and Sarah’s. Check in was so easy and they were very attentive to anything we needed. The property and apartment are beautiful, it was so nice waking up and seeing all the trees and it was so quiet. We will definitely be back and stay when we are visiting our daughter at Fairfield."
The price is AU$1,104
includes taxes & fees
26 Nov - 27 Nov
Westport Paradise With Every Amenity!

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

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

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

(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins

8.6 out of 10, Excellent, (4)
"The location of Ms. Jay's place is unbeatable! My group and I were in town for an event in the Total Mortgage Arena. The drive was 5 minutes max! Ms. Jay is great with communication. She was always available for any questions. The apartment is very homey, cozy and comfortable. Very nicely decorated and it has everything you might need. (We would just recommend some mirrors in the bedrooms). The place is next to a very busy street which there is always a lot of noise, especially at night. One...
(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins

Waterfront Cottage in Branford

10.0 out of 10, Exceptional, (87)
"The house was perfect for our annual getaway. We are a group of nine women who have been friends for over 45 years. The large well stocked kitchen with amazing view of the water and fireplace made our Friendsgiving meal memorable! The outdoor hot tub, fire pit, and deck with comfy seating topped off the weekend. Great location, plenty of parking, responsive host. 5/5 stars! "
Waterfront Cottage in Branford

Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.

Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.

Guesthouse at Norwalk Inn

3.5 star property
8.4 out of 10, Very good, (39)
"Great space would be better if there were kuerig cups to go with the machine in the kitchen"
The price is AU$489
includes taxes & fees
1 Dec - 2 Dec
Guesthouse at Norwalk Inn

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.

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.

Beachfront 3-bedroom vacation home just 14 minutes from Yale University

10.0 out of 10, Exceptional, (28)
"Very comfortable home. Perfect for our grown family. We enjoyed the relaxed atmosphere, the beach and water views right outside the back steps. We set up our umbrellas and chairs, had fun using the kyack and paddle board. It was a wonderful and relaxing time together! Looking forward to it again next year."
Beachfront 3-bedroom vacation home just 14 minutes from Yale University
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 types of properties in Stratford you may be interested in

Quality Suites

2.5 star property
7.6 out of 10, Good, (1070)
"None"
The price is AU$149
includes taxes & fees
22 Dec - 23 Dec
Quality Suites

Homewood Suites by Hilton Stratford

3.0 star property
8.8 out of 10, Excellent, (1020)
"Great property! There needs to be more tables at breakfast "
The price is AU$209
includes taxes & fees
20 Dec - 21 Dec
Homewood Suites by Hilton Stratford

The Surfside Hotel

2.0 star property
9.0 out of 10, Wonderful, (62)
"Cute motel, nice walkable area right by the sea."
The price is AU$287
includes taxes & fees
9 Dec - 10 Dec
The Surfside Hotel
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

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

Frequently asked questions

Are there holiday rentals in Stratford?

Yes, there are holiday rentals close to the most popular sights in Stratford, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and beaches in Stratford. Make sure you have time to check out the baseball games and shopping during your trip.

What are some of the best holiday rentals that Stratford has to offer?

Business or Weekend escape: This highly rated holiday home rental in Stratford is equipped with a BBQ, air conditioning and WiFi to help you feel comfortable during your stay. Kitchen amenities include a fridge, a microwave and a coffee maker.

How many holiday rentals are there in Stratford?

Choose from 10 Expedia holiday rentals in Stratford for a memorable holiday.

What can I see and do in Stratford?

Cultural attractions include Boothe Memorial Park and Museum and National Helicopter Museum, whereas Short Beach and Lordship Beach are a couple of picturesque spots to enjoy the outdoors. While here, Long Beach and Housatonic River are other places worth a visit.

What are holiday rentals like in Stratford?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Stratford. Holiday rentals feature amenities such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about cleanliness, a holiday rental can offer a sense of security away from public hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great choice for a family trip or a small group gathering.