Stratford Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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
The price is CA $126
CA $202 total
includes taxes & fees
Nov 11 - Nov 12
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, (118 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
The price is CA $244
CA $367 total
includes taxes & fees
Dec 8 - Dec 9
DUNE Fairfield Beach
A hotel lobby with a reception desk, seating area, and a large window providing a view of the outdoors.

3. 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 traveller
The price is CA $96
CA $110 total
includes taxes & fees
Nov 29 - Nov 30
Cozy 2-Bed ADA|Pool|Free Parking
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.
The price is CA $196
CA $313 total
includes taxes & fees
Nov 16 - Nov 17
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
A modern living room with a grey sofa, a glass coffee table, and large windows offering views of the street.

5. 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.
The price is CA $223
CA $363 total
includes taxes & fees
Nov 18 - Nov 19
Centric property close to all the great things in the city
A modern living room with a sofa, a coffee table with decorative items, and a large window with curtains.

6. 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
The price is CA $207
CA $567 total
includes taxes & fees
Nov 9 - Nov 10
Luxury Designer 2 bedroom+office/3bed vacation home.
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.
The price is CA $241
CA $609 total
includes taxes & fees
Nov 11 - Nov 12
Luxe, designer renovation; walk to Tyde wedding venue, shops & beach!
A kitchen with wooden cabinets, a stainless steel refrigerator, a dining table, and a sofa.

8. Elite room stay

Elite room stay
Bridgeport
The price is CA $290
CA $461 total
includes taxes & fees
Nov 11 - Nov 12
Elite room stay
A hotel lobby with a reception desk, seating area, and a large window providing a view of the outdoors.

9. Sunny 1 Full Bed ADA|Free parking

Sunny 1 Full Bed ADA|Free parking
MILFORD
10.0 out of 10, Exceptional, (4 reviews)
"Pool was clean and just right for a quick swim."
United States
Anonymous traveller
The price is CA $96
CA $110 total
includes taxes & fees
Nov 29 - Nov 30
Sunny 1 Full Bed ADA|Free parking
A room with a large arched window, a bed, a bedside table, a lamp, and a potted plant.

10. 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.
The price is CA $196
CA $313 total
includes taxes & fees
Nov 16 - Nov 17
Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk
A hotel lobby with a reception desk, seating area, and a large window providing a view of the outdoors.

11. 2 FULL BEDS | NON-SMOKING

2 FULL BEDS | NON-SMOKING
MILFORD
8.8 out of 10, Excellent, (5 reviews)
The price is CA $96
CA $110 total
includes taxes & fees
Nov 24 - Nov 25
2 FULL BEDS | NON-SMOKING
A modern kitchen with a white refrigerator, a stove, and a sink. There are four wicker chairs around a white table.

12. 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 traveller
The price is CA $172
CA $421 total
includes taxes & fees
Nov 30 - Dec 1
Renovated 2BR Retreat / Modern Comforts Included
A modern kitchen with wooden cabinets, a stainless steel sink, a microwave, a kettle, and a dish rack.

13. Modern 2 Bed in BlackRock

Modern 2 Bed in BlackRock
Black Rock Historic District
8.0 out of 10, Very good, (7 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.
The price is CA $203
CA $449 total
includes taxes & fees
Nov 8 - Nov 9
Modern 2 Bed in BlackRock
Private kitchen

14. 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
The price is CA $194
CA $481 total
includes taxes & fees
Nov 9 - Nov 10
The B&W Haven: Stylish 3BR Escape with Private Office by LI Ferry
A modern kitchen with white cabinets, a stainless steel refrigerator, a wooden island with a kettle, and a painting on the wall.

15. 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.
The price is CA $240
CA $540 total
includes taxes & fees
Nov 9 - Nov 10
Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
A beach with people sunbathing and walking along the shore, a pier with a covered area, and buildings in the background.

16. 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.
The price is CA $280
CA $772 total
includes taxes & fees
Nov 9 - Nov 10
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
Deck: Comfortable outdoor sofa sets for outdoor conversations

17. Serenity Haven: A Modern Retreat

Serenity Haven: A Modern Retreat
Monroe
9.8 out of 10, Exceptional, (6 reviews)
"My stay at the modern retreat in Monroe was perfect. Conveniently located near restaurants, supermarkets, banks Starbucks. Beautiful Wolfe Park is minutes away to enjoy a hike or a bike ride.The hosts were easily accessible with any questions and or concerns.This modern retreat won't disappoint."
United States
Tresha J.
The price is CA $154
CA $416 total
includes taxes & fees
Nov 9 - Nov 10
Serenity Haven: A Modern Retreat
A modern kitchen with white cabinets, a central island with bar stools, a microwave, and a dishwasher.

18. 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.
The price is CA $280
CA $772 total
includes taxes & fees
Nov 9 - Nov 10
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
A bedroom with two beds, a wooden dresser, and a mirror.

19. Cozy 1-bedroom house in welcoming Bridgeport

Cozy 1-bedroom house in welcoming Bridgeport
Bridgeport
The price is CA $431
CA $644 total
includes taxes & fees
Nov 9 - Nov 10
Cozy 1-bedroom house in welcoming Bridgeport
A two-story house with a porch, stone steps, and a variety of plants.

20. 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.
The price is CA $921
CA $1,738 total
includes taxes & fees
Nov 9 - Nov 10
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
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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Find vacation rentals that suit your style

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Top Stratford Hotel Reviews

A building entrance with a stone facade, a wooden archway, and a large glass door.
Homewood Suites by Hilton Stratford

Homewood Suites by Hilton Stratford

Homewood Suites by Hilton Stratford
Stratford

10/10 Excellent

Very close if you are visiting Sikorsky across the road. Decent pool and a nice free hot breakfast in the lobby.
Canada
Allan
Reviewed May 4, 2025
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, cottages, cabins, villas... 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Stratford vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Stratford vacation rentals we have selected for you start as low as CA $95 per night. Entering your travel dates in the search wizard 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.