A beach with rippled sand patterns and a sunset sky.

Stratford Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Stratford vacation rentals

Pool

1. Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (59 reviews)
"Definitely clean - good place for an overnight stay."
United States
Kimberly
$135 nightly
The price is $152
Oct 5 - Oct 6
Total with taxes and fees
Business or Weekend escape
Classic Suite | Iron/ironing board, WiFi (free), bed sheets

2. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (113 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
$235 nightly
The price is $270
Sep 28 - Sep 29
Total with taxes and fees
DUNE Fairfield Beach
1 bedroom, desk, iron/ironing board, WiFi (free)

3. Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
Downtown Bridgeport
9.4 out of 10, Exceptional, (18 reviews)
"The accommodations were incredible. The host provided many helpful materials that made the stay very comfortable. The apartment was very cute and had nice amenities for the guests that go above any beyond what a hotel can provide."
United States
Bailey
$205 nightly
The price is $232
Sep 23 - Sep 24
Total with taxes and fees
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
Interior

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

Luxury Designer 2 bedroom+office/3bed vacation home.
Brooklawn - St. Vincent
9.6 out of 10, Exceptional, (27 reviews)
"Very accurate description of listing - host was very responsive. Would stay again!"
United States
Anonymous traveler
$313 nightly
The price is $356
Sep 22 - Sep 23
Total with taxes and fees
Luxury Designer 2 bedroom+office/3bed vacation home.
Interior

5. Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
Downtown Bridgeport
9.6 out of 10, Exceptional, (12 reviews)
"Perfect option for a quick visit, Would stay again!"
United States
Destiny
$171 nightly
The price is $194
Oct 5 - Oct 6
Total with taxes and fees
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
Dining

6. Luxe, designer renovation; walk to Tyde wedding venue, shops & beach!

Luxe, designer renovation; walk to Tyde wedding venue, shops & beach!
Milford
9.8 out of 10, Exceptional, (9 reviews)
"Very comfortable modern home, clean, great backyard, pet friendly Host was so accommodating and responsive, personal note at check-in "
United States
Traci F.
$400 nightly
The price is $453
Sep 24 - Sep 25
Total with taxes and fees
Luxe, designer renovation; walk to Tyde wedding venue, shops & beach!
Smart TV

7. Centric property close to all the great things in the city

Centric property close to all the great things in the city
Brooklawn - St. Vincent
6.6 out of 10, (17 reviews)
"This rental was great accommodation"
United States
Alma B.
$226 nightly
The price is $257
Sep 22 - Sep 23
Total with taxes and fees
Centric property close to all the great things in the city
Coffee/tea maker, fridge, microwave, oven

8. Renovated 2BR Retreat / Modern Comforts Included

Renovated 2BR Retreat / Modern Comforts Included
West End - West Side
10.0 out of 10, Exceptional, (3 reviews)
"We had an awesome time staying Here Everything was super clean And the communication with the host was great we would greatly recommend would definitely stay again!"
United States
Anonymous traveler
$288 nightly
The price is $326
Oct 6 - Oct 7
Total with taxes and fees
Renovated 2BR Retreat / Modern Comforts Included
1 bedroom, desk, iron/ironing board, WiFi (free)

9. Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk

Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk
Downtown Bridgeport
9.4 out of 10, Exceptional, (8 reviews)
"The Orange & Groovy Apt. was as described. All the amenities we needed and we had a lovely time and enjoyed the area. Will book again!"
United States
Betty W.
$205 nightly
The price is $232
Sep 24 - Sep 25
Total with taxes and fees
Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk
Coffee/tea maker, fridge, microwave, oven

10. The B&W Haven: Stylish 3BR Escape with Private Office by LI Ferry

The B&W Haven: Stylish 3BR Escape with Private Office by LI Ferry
Brooklawn - St. Vincent
$344 nightly
The price is $390
Oct 6 - Oct 7
Total with taxes and fees
The B&W Haven: Stylish 3BR Escape with Private Office by LI Ferry
Private kitchen

11. Elite room stay

Elite room stay
Bridgeport
$289 nightly
The price is $329
Sep 22 - Sep 23
Total with taxes and fees
Elite room stay
1 bedroom, desk, iron/ironing board, WiFi

12. One bedroom in United States of America, New Haven

One bedroom in United States of America, New Haven
Dwight
9.0 out of 10, Wonderful, (2 reviews)
"We enjoyed our stay. The accommodations were clean and spacious and communication was quick and helpful. Would definitely come back!"
United States
Rosanne M.
$165 nightly
The price is $187
Sep 27 - Sep 28
Total with taxes and fees
One bedroom in United States of America, New Haven
Terrace/patio

13. Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio

Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
Tunxis Hill
10.0 out of 10, Exceptional, (2 reviews)
"Host was attentive and the space was comfortable and exactly what we needed"
United States
Parker M.
$288 nightly
The price is $328
Sep 22 - Sep 23
Total with taxes and fees
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
Beach nearby, sun loungers, beach towels

14. Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train

Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
Fairfield
10.0 out of 10, Exceptional, (39 reviews)
"Great accommodations and perfect location for us. "
United States
Kim G.
$525 nightly
The price is $594
Oct 21 - Oct 22
Total with taxes and fees
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
Coffee/tea maker, fridge, microwave, oven

15. Modern 2 Bed in BlackRock

Modern 2 Bed in BlackRock
Black Rock Historic District
7.6 out of 10, Good, (5 reviews)
"Cute and efficient property, and a great location. The host was very prompt with any and all questions. Definitely recommend the place for a quick get away."
United States
Joshua L.
$282 nightly
The price is $321
Sep 22 - Sep 23
Total with taxes and fees
Modern 2 Bed in BlackRock
Coffee/tea maker, fridge, oven, stovetop

16. Serene Country Cottage

Serene Country Cottage
Woodbridge
8.0 out of 10, Very good, (11 reviews)
"We had a great one night stay here! The place is really cute, clean and comfortable. One of the greatest parts about the stay was the host, Trent. He was welcoming and VERY responsive to questions! "
United States
felicia
$180 nightly
The price is $204
Sep 23 - Sep 24
Total with taxes and fees
Serene Country Cottage
Dining

17. Spacious 2 Bedroom apartment close to Yale Bowl

Spacious 2 Bedroom apartment close to Yale Bowl
West New Haven
9.6 out of 10, Exceptional, (79 reviews)
"Clean, thoughtful, safe. Great stay"
United States
Daniel S.
$187 nightly
The price is $212
Sep 22 - Sep 23
Total with taxes and fees
Spacious 2 Bedroom apartment close to Yale Bowl
Exterior

18. Angelica’s safe haven @ west haven

Angelica’s safe haven @ west haven
West Haven
10.0 out of 10, Exceptional, (8 reviews)
"We had a great stay. Comfortable home with a large living room. Beds were great. "
United States
Jason V.
$296 nightly
The price is $335
Sep 22 - Sep 23
Total with taxes and fees
Angelica’s safe haven @ west haven
Coffee/tea maker, fridge, microwave, oven

19. Stylish Westville Apartment near Yale Campus

Stylish Westville Apartment near Yale Campus
West New Haven
8.8 out of 10, Excellent, (3 reviews)
"Convenient location & hosts"
United States
Northeast C.
$218 nightly
The price is $247
Sep 22 - Sep 23
Total with taxes and fees
Stylish Westville Apartment near Yale Campus
1 bedroom, desk, WiFi, bed sheets

20. Spacious Studio with Pool Table

Spacious Studio with Pool Table
Westport
8.6 out of 10, Excellent, (7 reviews)
"The room was great, the location was good and there was a pool table! "
United States
Eadweard
$226 nightly
The price is $246
Sep 22 - Sep 23
Total with taxes and fees
Spacious Studio with Pool Table
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.
View all properties
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

Homewood Suites by Hilton Stratford

Homewood Suites by Hilton Stratford

8/10 Good
"I read a review that the venue was new, maybe they meant newly renovated. I has a queen bed suite. which was perfect for 1 or 2 people. the room was clean but could use a new carpet. the dining hall and patio were inviting. Just wish there was a hot tub in the pool area. Staff was welcoming and helpful. It was the perfect place for a quiet get away. waffle batter needs a bit more flavor. LTB"
Linda 1-night trip
Posted 9 hours ago
Homewood Suites by Hilton Stratford

Find out more about Stratford

Everything you need to know about Stratford vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Stratford vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Stratford vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Stratford vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Stratford. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Stratford in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $152 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Stratford rentals

At Expedia, we put the best Stratford vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Stratford rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Stratford vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Stratford. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Stratford?

Yes, you can find vacation rentals close to popular sights in Stratford, or you can go with a more secluded option if you'd like a relaxing place to 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's the top vacation rental that Stratford has to offer?

Business or Weekend escape: This Stratford vacation home rental offers a garden, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave, and a coffee maker.

How many vacation rentals are there in Stratford?

Choose from 14 Expedia vacation rentals in Stratford for a memorable vacation.

What can I see and do in Stratford?

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

What are vacation rentals like in Stratford?

Vacation rentals are private properties you can stay in for a few days or a quick weekend in Stratford. Vacation rentals provide amenities like laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, vacation rentals can provide a sense of security away from public hotel elevators and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for small groups.