Stratford Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Stratford vacation rentals

A swimming pool at night with blue lighting.

1. Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (60 reviews)
"Definitely clean - good place for an overnight stay."
United States
Kimberly
$127 nightly
The price is $144
Nov 11 - Nov 12
Total with taxes and fees
Business or Weekend escape
A modern kitchen with white cabinets, a dining area with wooden chairs, a large window, and a view of the city.

2. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (119 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
$235 nightly
The price is $270
Nov 22 - Nov 23
Total with taxes and fees
DUNE Fairfield Beach
A modern living room with a sofa, a coffee table with decorative items, and a large window with curtains.

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

Luxury Designer 2 bedroom+office/3bed vacation home.
Brooklawn - St. Vincent
9.4 out of 10, Exceptional, (29 reviews)
"Great location and clean property. Some items were broken or missing, but overall, a nice stay."
United States
Cherie
$355 nightly
The price is $404
Nov 16 - Nov 17
Total with taxes and fees
Luxury Designer 2 bedroom+office/3bed vacation home.
A bedroom with a large arched window, a bed, a bedside table with a lamp, and a small seating area with cushions and a plant.

4. 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, (19 reviews)
"A hidden gem! We have stayed here twice now when attending concerts at Hartford Healthcare Amphitheater. A beautifully appointed room within walking distance to the shows!"
United States
Kim F.
$195 nightly
The price is $222
Nov 16 - Nov 17
Total with taxes and fees
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
A modern kitchen with a white refrigerator, a stove, and a sink. There are four wicker chairs around a white table.

5. 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
$262 nightly
The price is $298
Nov 11 - Nov 12
Total with taxes and fees
Renovated 2BR Retreat / Modern Comforts Included
Private kitchen

6. 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
10.0 out of 10, Exceptional, (1 review)
"."
United States
Matthew R.
$299 nightly
The price is $341
Nov 11 - Nov 12
Total with taxes and fees
The B&W Haven: Stylish 3BR Escape with Private Office by LI Ferry
A modern kitchen with a marble island, bar stools, and a dining area with a table and chairs.

7. 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, (10 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.
$379 nightly
The price is $432
Nov 11 - Nov 12
Total with taxes and fees
Luxe, designer renovation; walk to Tyde wedding venue, shops & beach!
A modern living room with a grey sofa, a glass coffee table, and large windows offering views of the street.

8. 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
6.8 out of 10, (18 reviews)
"This rental was great accommodation"
United States
Alma B.
$225 nightly
The price is $256
Nov 21 - Nov 22
Total with taxes and fees
Centric property close to all the great things in the city
A hotel lobby with a reception desk, seating area, and a large window providing a view of the outdoors.

9. Cozy 2-Bed ADA|Pool|Free Parking

Cozy 2-Bed ADA|Pool|Free Parking
MILFORD
10.0 out of 10, Exceptional, (4 reviews)
"Would tell anyone passing through to stop here if they want quick check-in and restful sleep quality. Parking is easy to find close by, so no hassle with unloading bags."
United States
Anonymous traveler
$68 nightly
The price is $79
Nov 29 - Nov 30
Total with taxes and fees
Cozy 2-Bed ADA|Pool|Free Parking
A kitchen with wooden cabinets, a stainless steel refrigerator, a dining table, and a sofa.

10. Elite room stay

Elite room stay
Bridgeport
$288 nightly
The price is $328
Nov 11 - Nov 12
Total with taxes and fees
Elite room stay
A modern living room with a black leather sofa, a coffee table, and a TV stand. There is a staircase leading to another level.

11. 171 Broadway · Renovated House Steps Away From The Ocean

171 Broadway · Renovated House Steps Away From The Ocean
Milford
8.4 out of 10, Very good, (8 reviews)
"very clean, new and great location! Will book again."
United States
ScottTakacs a.
$393 nightly
The price is $393
Nov 15 - Nov 16
Total with taxes and fees
171 Broadway · Renovated House Steps Away From The Ocean
A two-story house with a blue exterior, a front porch, and a driveway leading to the entrance.

12. Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
$1,452 nightly
The price is $1,669
Dec 11 - Dec 12
Total with taxes and fees
Beechmont - Perfect for Family Retreat!
A two-story house with a porch, stone steps, and a variety of plants.

13. Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
North End
8.8 out of 10, Excellent, (10 reviews)
"Plenty of bedrooms and space for the family. Very prompt communication with host."
United States
David K.
$1,090 nightly
The price is $1,241
Nov 11 - Nov 12
Total with taxes and fees
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
A modern kitchen with white cabinets, a stainless steel refrigerator, a wooden island with a kettle, and a painting on the wall.

14. Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch

Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
West End - West Side
9.6 out of 10, Exceptional, (5 reviews)
"Nice place to stay "
United States
Maria Elena G.
$317 nightly
The price is $361
Nov 11 - Nov 12
Total with taxes and fees
Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
A staircase with white balusters, a wicker chair, a lamp, and a television mounted on the wall.

15. 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, (41 reviews)
"Great accommodations and perfect location for us. "
United States
Kim G.
$480 nightly
The price is $547
Nov 11 - Nov 12
Total with taxes and fees
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
A cozy room with a sectional sofa, a small table, and a window with a view of trees.

16. Downtown 2br/1ba apartment -- free parking, outdoor patio & walk everywhere

Downtown 2br/1ba apartment -- free parking, outdoor patio & walk everywhere
Milford
9.6 out of 10, Exceptional, (4 reviews)
"Great location and well appointed"
United States
Greg G.
$496 nightly
The price is $565
Nov 11 - Nov 12
Total with taxes and fees
Downtown 2br/1ba apartment -- free parking, outdoor patio & walk everywhere
A modern kitchen with white cabinets, stainless steel appliances, a wooden island, and a painting on the wall.

17. Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious

Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
Tunxis Hill
9.6 out of 10, Exceptional, (22 reviews)
"The house is very clean and spacious! Great location for what my party needed. The host is incredibly responsive and very helpful. Overall this was a fantastic stay and would recommend. "
United States
Emily K.
$674 nightly
The price is $768
Nov 11 - Nov 12
Total with taxes and fees
Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
A hotel entrance with a covered walkway, a prominent tower, and a well-lit facade.

18. Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"it was amazing will stay again food was good comfort was great "
United States
anthony
$298 nightly
The price is $343
Dec 2 - Dec 3
Total with taxes and fees
Guesthouse at Norwalk Inn
A room with a large arched window, a bed, a bedside table, a lamp, and a potted plant.

19. 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, (9 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.
$195 nightly
The price is $222
Nov 16 - Nov 17
Total with taxes and fees
Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk
A modern kitchen with white cabinets, a central island with bar stools, a microwave, and a dishwasher.

20. Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train

Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
Fairfield
10.0 out of 10, Exceptional, (19 reviews)
"Beautiful home, clean and exactly as described.We loved our stay and plan on returning.The host was wonderful to work with.An overall excellent experience."
United States
Tara C.
$480 nightly
The price is $547
Nov 11 - Nov 12
Total with taxes and fees
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
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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Top Stratford Hotel Reviews

A modern living room with geometric-patterned furniture, large windows, and a minimalist design.
Delamar Westport

Delamar Westport

Delamar Westport
Westport

10/10 Excellent

Pool and sauna were an excellent part of the experience. Breakfast buffet was top notch. The moment we arrived, the valet crew and front desk staff made me feel completely relaxed. I knew instantly that I made the right choice booking a stay at Delamar.
United States
James
Reviewed November 9, 2026
Delamar Westport

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 $78 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.

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 Lordship Beach and Housatonic River are a couple of picturesque spots to enjoy the outdoors. While here, Perry House and Stratford Speedway 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.

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