A pebbled beach at sunset with the ocean and a distant city skyline.

Stratford Vacation Rentals

Q: 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.

Where to?

Dates

November 2026

December 2026

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Our top choices for Stratford vacation rentals

A swimming pool at night with blue lighting.

1. Business or Weekend escape

Stratford

Kimberly

$127 nightly

Nov 12 - Nov 13

Total with taxes and fees

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

Fairfield Beach

slava

$235 nightly

Nov 22 - Nov 23

Total with taxes and fees

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.

Brooklawn - St. Vincent

Cherie

$355 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

Downtown Bridgeport

Kim F.

$195 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

West End - West Side

Anonymous traveler

$262 nightly

Nov 12 - Nov 13

Total with taxes and fees

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

Brooklawn - St. Vincent

Matthew R.

$299 nightly

Nov 12 - Nov 13

Total with taxes and fees

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!

Milford

Traci F.

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

Brooklawn - St. Vincent

Alma B.

$225 nightly

Nov 18 - Nov 19

Total with taxes and fees

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

MILFORD

Anonymous traveler

$68 nightly

Nov 29 - Nov 30

Total with taxes and fees

A kitchen with wooden cabinets, a stainless steel refrigerator, a dining table, and a sofa.

10. Elite room stay

Bridgeport

$288 nightly

Nov 12 - Nov 13

Total with taxes and fees

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

Milford

ScottTakacs a.

$393 nightly

Nov 12 - Nov 13

Total with taxes and fees

A two-story house with a blue exterior, a front porch, and a driveway leading to the entrance.

12. Beechmont - Perfect for Family Retreat!

North End

$1,369 nightly

Nov 13 - Nov 14

Total with taxes and fees

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!

North End

David K.

$1,098 nightly

Nov 18 - Nov 19

Total with taxes and fees

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

West End - West Side

Maria Elena G.

$318 nightly

Nov 18 - Nov 19

Total with taxes and fees

A beach with people sunbathing and walking along the shore, a pier with a covered area, and buildings in the background.

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

Fairfield

Kim G.

$480 nightly

Nov 12 - Nov 13

Total with taxes and fees

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

Milford

Greg G.

$477 nightly

Nov 12 - Nov 13

Total with taxes and fees

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

Tunxis Hill

Emily K.

$674 nightly

Nov 12 - Nov 13

Total with taxes and fees

A hotel entrance with a covered walkway, a prominent tower, and a well-lit facade.

18. Guesthouse at Norwalk Inn

Historic District

anthony

$298 nightly

Dec 2 - Dec 3

Total with taxes and fees

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

Downtown Bridgeport

Betty W.

$195 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

Fairfield

Tara C.

$480 nightly

Nov 12 - Nov 13

Total with taxes and fees

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Find vacation rentals that suit your style

Top Stratford Hotel Reviews

A buffet bar with various food items and a selection of liquor bottles in the background.

Delamar Westport

Westport

10/10 Excellent

James

An outdoor patio with a fire feature, seating, and a building with large windows and a stone facade.

Home2 Suites by Hilton East Haven New Haven

The Centre

10/10 Excellent

Daniel

A spacious living area with a dining table, comfortable seating, and a large window providing natural light.

Residence Inn by Marriott Milford

Milford

10/10 Excellent

Jeffrey

A stone building with a covered patio area, outdoor seating, and a fire feature.

Homewood Suites by Hilton Orange New Haven

Orange

10/10 Excellent

Meyra

A modern building entrance with a covered walkway, a white car parked in front, and two people near the entrance.

Hotel Marcel New Haven, Tapestry Collection By Hilton

Long Wharf

10/10 Excellent

Matthew

A building entrance with a stone facade, a wooden archway, and a large glass door.

Homewood Suites by Hilton Stratford

Stratford

10/10 Excellent

Starr

A modern restaurant with a bar area, seating arrangements, and a decorative wall.

The Blake Hotel

Downtown New Haven

10/10 Excellent

Robert

A library with bookshelves, a sofa, a lamp, and decorative items.

The Study at Yale

Downtown New Haven

10/10 Excellent

We truly had a terrific experience. We drove New Jersey with my granddaughter who is doing her sevond Master’s Degree in Scotland. She needed Research materials at the Yale Library. We arrived at The Study at 10 am instead of the 3 pm check in. The front desk clerks were exceptional and said our rooms were ready! The breakfast and dinner we had in the Study restaurant were delicious. The two king rooms were clean and large with a desk and a large leather chair and haddock. We were very...

Gregory

A hotel entrance with a covered patio, a glass door entrance, and a landscaped area with shrubs.

Hilton Garden Inn Milford

Milford

10/10 Excellent

Hotel was nice. Pros: location, free parking, clean, microwave and fridge, free water, pool, staff friendly, nice size bathroom and also a nice size bathroom at entrance, coffee and tea was out in morning Cons: no free breakfast. Pillows; my sister said her pillows were to soft. I found them quite nice. Seems to be a preference. The Tv was rather small for two queen beds to share (around 30 inches). Area: Milford beach parking is $40 and beach wasn’t special. Wood mount beach FREE street...

Jade

A reception area with a wooden reception desk, a checkered floor, a framed portrait, and a bulletin board with pins.

Graduate by Hilton New Haven

Downtown New Haven

10/10 Excellent

Anonymous traveler

A modern lobby with leather sofas, a wooden reception desk, and a large abstract art piece on the wall.

Hyatt Place Milford / New Haven

Milford

10/10 Excellent

Robin

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.

Stratford Vacation Rentals

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Upfront pricing

Check prices for these dates

Our top choices for Stratford vacation rentals

1. Business or Weekend escape

2. DUNE Fairfield Beach

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

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

5. Renovated 2BR Retreat / Modern Comforts Included

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

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

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

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

10. Elite room stay

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

12. Beechmont - Perfect for Family Retreat!

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

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

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

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

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

18. Guesthouse at Norwalk Inn

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

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

Find vacation rentals that suit your style

Top Stratford Hotel Reviews

Delamar Westport

10/10 Excellent

Find out more about Stratford

Everything you need to know about Stratford vacation rentals

Stratford vacation rentals: An excellent choice for every season

How to find incredible deals on Stratford rentals

Frequently Asked Questions

Are there vacation rentals in Stratford?

What's the top vacation rental that Stratford has to offer?

How many vacation rentals are there in Stratford?

What can I see and do in Stratford?

What are vacation rentals like in Stratford?

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