Vacation rentals in Stratford

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Top-rated vacation rentals in Stratford

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Guest favorite

Guest suite in Fairfield

4.92 out of 5 average rating, 109 reviews

Suite; 1 Bedroom & Living Area/Xtra Bedrm; Kitchen

Fully accessorized, large (1,255 sq ft) beautiful suburban space consisting of bedroom (queen), an exclusive-use living room/extra bedroom with twin pull-out bed, private full bath; in-unit washer/dryer; for stays of 1 week or less: exclusive use of main kitchen; private entrance to space. Includes continental breakfast, 2 large-screen TVs. Unit on the ground floor of a 3 story home. Owners on property. Train station about a mile away (NYC: 70 minutes). Easy walk to Fairfield University.

Feb 24 – Mar 3

$102 per night

Guest favorite

Apartment in Milford

4.94 out of 5 average rating, 107 reviews

The Boathouse, private downtown Harborside suite

The Boathouse is a detached one bedroom studio apartment situated behind our home in the heart of Historic downtown Milford. Through a private entrance you will discover a thoughtfully furnished bedroom (queen bed & pull out couch), dining room, full kitchen & bath. It is ideally suited for a couple/small family looking for a memorable beachtown getaway. Walk, rent bikes/kayaks, shop, dine, enjoy art, music, or a day at the beach… our quintessential New England seaside town is sure to charm you!

Sep 28 – Oct 5

$176 per night

Guest favorite

Guest suite in Fairfield

4.93 out of 5 average rating, 110 reviews

Adorable private apt w/ W/D in lovely neighborhood

Enjoy a lovely experience at this centrally-located studio in-law apartment. It boasts a newly renovated kitchen and bath, king bed with brand new mattress, pull out full size sofa, ample closet space and more. The eat-in kitchen has all you need to feel right at home. The apartment is located adjacent to a nice residential house, but is fully private with your own front and back entrances. There are also no stairs, making it easily accessible. It’s located in a wonderful neighbor in Fairfield.

Nov 27 – Dec 4

$122 per night

Guest favorite

Apartment in Milford

4.97 out of 5 average rating, 508 reviews

Water front studio apartment with fireplace.

This is a beautifully appointed studio apartment located off the patio level of a water front home. Guests enjoy a large private patio over looking gorgeous sweeping views of Long Island Sound. A private entrance and off street parking. The amazing views and amenities make this space the perfect romantic getaway! Close to I95 and Metro North railroad. Ten minutes to great dining in downtown Milford. A true waterfront oasis! Come and experience this beautiful retreat! You won't be disappointed!

Sep 26 – Oct 3

$175 per night

Guest favorite

Apartment in Bridgeport

5.0 out of 5 average rating, 6 reviews

Ricport Studio 5

This little studio is the perfect shut in. An electric fire place, with a curved smart TV, complimented by handmade industrial colored windows, makes this place dangerous for letting time fly. To help the space open up, we installed a Murphy bed (that should be handled with care). Theres no doubt you’ll feel comfortable and at home as soon as you arrive. Located 2min from Metro North/Amtrak, 4min from Port Jeff. ferry, 5min from Arena/Theater, 6min Park/Beach, Downtown, near it all. Ask Parking

Apr 22 – 29

$75 per night

Guest favorite

Home in Milford

4.98 out of 5 average rating, 153 reviews

Designer Beach Retreat on Exclusive Cedar Beach

Welcome to your own slice of heaven! Enjoy dinner in your Chef's kitchen while watching one of the most radiant sunsets you will ever see. Stunning views from the private rear deck or snuggled on the couch inside the living room. Wade into Long Island Sound with semi-private beach access 250 feet away. The property is 5 doors down from the CT Audubon Society, known for its epic views and wildlife watching. The sunrises & sunsets are beautiful! 15 minutes to Yale. We can't wait to host you!

Nov 2 – 9

$273 per night

Guest favorite

Cottage in Easton

4.98 out of 5 average rating, 190 reviews

Cozy Modern Cottage with Fireplace

Clean, modern + large, our guest house has all the amenities and comforts of home. Cottage is dressed in whites and neutrals with natural light and plants throughout for a sacred, restful feel. Full kitchen, king bed, gas fireplace, laundry and spacious grounds with meditation hill, fire pit, stone fences, and nearby hiking trails. Pool and hot tub May-Sept. Come relax in New England's stunning natural beauty. Read our photo captions for more details. We look forward to meeting you!

May 6 – 13

$108 per night

Guest favorite

Guesthouse in Milford

5.0 out of 5 average rating, 32 reviews

The studio downtown

The studio is a new, private, quiet, and peaceful space. It is situated on the second floor of a detached garage with a private entrance. It is located in the historic center of town, within walking distance of the train station, bars, restaurants, and beach. It is ideal for a couple looking for a beach town getaway. The studio has a king-size bed, an eating area, a kitchenette with a fridge, a sink, a double induction cooktop, a seating area, and a bathroom with a rain shower.

Jan 21 – 28

$114 per night

Guest favorite

Cottage in Milford

4.96 out of 5 average rating, 235 reviews

Spring Sale! Cozy Cottage | Walk to Beach | Pet

Inspired by my Dad's wanderlust and love of sea & sand. Relax and unwind in this completely remodeled, stylish Cottage a block and a half from Long Island Sound and .9 mile to Walnut Beach - walk to coffee, pizza, lobster shack! We offer a modern kitchen, breakfast nook, dining area, natural stone wall, parking and W/D. Located in a charming coastal town - enjoy quiet neighborhood walks, coastal trails, boardwalk, breweries and restaurants. 15 min to Yale/New Haven, 65 mi to NYC.

Oct 11 – 18

$210 per night

Guest favorite

Home in Stratford

4.93 out of 5 average rating, 101 reviews

Quaint Colonial - Private Hot Tub & Entire House

The way Airbnb used to be, something special... a home away from home. No long rule book, just be respectful. Come and stay in this cozy colonial home centrally located in Stratford CT. Walk to the park, soak in the spa (during cold weather it's the BEST), sip tea, listen to music, play games, and relax. Less than 10 minutes from some of the best CT has to offer - beaches, shopping, restaurants, grocery, entertainment, hiking, train to NYC / Yale, and more.

Sep 3 – 10

$229 per night

Guest favorite

Apartment in Brookfield

4.94 out of 5 average rating, 184 reviews

Peaceful apartment on 3.5 acres w/ Artist studio.

Welcome to our cozy apartment! This fully enclosed apartment is attached to our main house on a beautiful 3.5-acre property in Brookfield. Enjoy a kitchen, comfortable living and bedroom area, and a clean bathroom. Guests have access to a shared 32 ft, 10 ft deep pool, artist studio, pool table,, garden, fire space, and outdoor seating. We provide a guidebook for your convenience. Book now and experience a perfect blend of comfort, creativity, and relaxation.

Sep 13 – 20

$101 per night

Guest favorite

Guest suite in Milford

5.0 out of 5 average rating, 14 reviews

Modern Studio & Gamers Paradise Near Downtown

Discover endless fun at our game-filled retreat! Choose from a variety of board games, enjoy a game of bumper pool or darts, and dive into the world of video games. Minutes from Silver Sands Beach, downtown Milford, and main highways, this spacious studio features a workout area, dedicated workspace, full bathroom, kitchenette, and open layout. Perfect for a fun-filled getaway, our home ensures a blend of relaxation and entertainment in a prime location!

Feb 24 – Mar 3

$106 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Stratford vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Stratford's top sights

LA Fitness13 locals recommend

Joey C's Boathouse Cantina & Grill7 locals recommend

Bridgeport Flyer Diner3 locals recommend

ShopRite of Shelton3 locals recommend

Whiskey Barrel5 locals recommend

Riverview Bistro Restaurant & Banquet Facility7 locals recommend

Other great vacation rentals in Stratford

Guest favorite

Loft in Milford

4.94 out of 5 average rating, 95 reviews

Lovely water front lower-level loft, free parking

Jan 29 – Feb 5

$109 per night

Guest favorite

Apartment in Stratford

4.99 out of 5 average rating, 94 reviews

2-Bedroom 1st floor unit 7 minutes from beach

Jul 27 – Aug 3

$247 per night

Guest favorite

Apartment in Bridgeport

5.0 out of 5 average rating, 6 reviews

Beautiful Apartment Quiet Area

May 9 – 16

$97 per night

Superhost

Home in Stratford

4.83 out of 5 average rating, 12 reviews

The Rose

Nov 14 – 21

$142 per night

Guest favorite

Apartment in Fairfield

4.95 out of 5 average rating, 62 reviews

Sunny Fairfield Studio Apartment

Oct 7 – 14

$124 per night

Guest favorite

Tiny home in Milford

4.96 out of 5 average rating, 53 reviews

Beach Cabana

Oct 13 – 20

$125 per night

Guest favorite

Apartment in Milford

5.0 out of 5 average rating, 48 reviews

The Pond Mill Retreat w/ 2 Bdrms & Pool

Sep 3 – 10

$147 per night

Guest favorite

Apartment in Milford

4.95 out of 5 average rating, 75 reviews

Downtown, Private balcony, 1gb fiber Wi-Fi

May 2 – 9

$131 per night

Show all

Quick stats about vacation rentals in Stratford

Total rentals
150 properties
Rentals with dedicated workspaces
100 properties have a dedicated workspace
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
50 properties allow pets
Family-friendly rentals
100 properties are a good fit for families
Total number of reviews
4K reviews

Frequently Asked Questions

Where should I stay in Stratford?
Make yourself at home in Stratford by choosing from our most frequently booked neighborhoods. We have over 160 vacation rentals in Stratford Center Historic District, over 160 vacation rentals in Boston Ave - Mill Hill, and over 160 vacation rentals in Lordship.
Do apartment rentals in Stratford have air conditioning?
Absolutely! We offer over 10 apartment rentals with air conditioning in Stratford. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Cottage Rentals in Stratford?
Enhance your stay in our Cottage Rentals with the most popular amenities: over 10 homes with a kitchen, over 10 homes with free parking, over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do apartment rentals in Stratford have free parking?
Absolutely! We offer over 10 apartment rentals with free parking in Stratford. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Stratford?
Yes! Work meets play with ease at over 100 vacation rentals in Stratford featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do cottage rentals in Stratford have a kitchen?
Absolutely! We offer over 10 cottage rentals with a kitchen in Stratford. Enjoy a tailored experience with all the comforts you desire.
Are there Stratford vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Stratford, available on Airbnb. Make a splash and soak up the sun in style!
Do apartment rentals in Stratford have wifi?
Absolutely! We offer over 20 apartment rentals with wifi in Stratford. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Stratford?
Stratford has more than 100 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there pet-friendly vacation rentals in Stratford?
Four-legged friends are welcome in Stratford. Choose from more than 50 vacation rentals for guests traveling with pets.

Vacation rentals in Stratford

Top-rated vacation rentals in Stratford

Vacation rentals for every style

Houses

Apartments

Hotels

Popular amenities for Stratford vacation rentals

Stay near Stratford's top sights

Other great vacation rentals in Stratford

Loft in Milford

Apartment in Stratford

Apartment in Bridgeport

Home in Stratford

Apartment in Fairfield

Tiny home in Milford

Apartment in Milford

Apartment in Milford

Quick stats about vacation rentals in Stratford

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Where should I stay in Stratford?

Do apartment rentals in Stratford have air conditioning?

What are the most popular amenities for Cottage Rentals in Stratford?

Do apartment rentals in Stratford have free parking?

Are there vacation rentals with a dedicated workspace in Stratford?

Do cottage rentals in Stratford have a kitchen?

Are there Stratford vacation rentals on Airbnb with pools?

Do apartment rentals in Stratford have wifi?

Are there family-friendly vacation rentals in Stratford?

Are there pet-friendly vacation rentals in Stratford?

Destinations to explore