Holiday rentals in Stratford

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Top-rated holiday rentals in Stratford

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Guest favourite

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.

24–31 Oct

£113 per night

Guest favourite

Flat in Milford

4.94 out of 5 average rating, 106 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!

29 Oct – 5 Nov

£190 per night

Guest favourite

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.

24 Nov – 1 Dec

£138 per night

Guest favourite

Flat 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!

25 Sept – 2 Oct

£191 per night

Guest favourite

Loft in Milford

4.94 out of 5 average rating, 94 reviews

Lovely water front lower-level loft, free parking

This unique centrally located water front loft is located on the second Gulf Pond 1.5 miles from historic Milford center buzzing with water front restaurants and downtown shopping. This one bedroom, one bath, has a private entrance and free off street parking. Outdoor patio & grill with kitchenette, enjoy a waterfront view throughout the 400 sq ft space. Close to I-95, the Merrit Parkway, and Milford train station. Explore 17 miles of beaches in this New England town by bike, kayak, or foot.

28 Feb – 7 Mar

£121 per night

Guest favourite

Home in Milford

4.98 out of 5 average rating, 152 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!

11–18 Oct

£312 per night

Guest favourite

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!

2–9 May

£147 per night

Guest favourite

Guest house in Milford

5.0 out of 5 average rating, 31 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.

18–25 Jan

£127 per night

Guest favourite

Cottage in Milford

4.96 out of 5 average rating, 233 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.

15–22 Jun

£236 per night

Guest favourite

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.

3–10 Sept

£255 per night

Guest favourite

Flat in Brookfield

4.94 out of 5 average rating, 183 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.

26 Sept – 3 Oct

£112 per night

Superhost

Loft in Bridgeport

4.86 out of 5 average rating, 173 reviews

Cozy Loft in beautiful St. Mary's by the Sea

Renovated cozy loft in beautiful St. Mary's by The Sea in Black Rock. Walking distance to award winning restaurants. Easy access to NYC/New Haven Metro North transit. Perfect for a weekend at the beach. Property includes 1 bed and a 78” sofa. Fully equipped kitchen with all major appliances, WiFi, & large TV. ***Please note that the ceilings are angled so taller guests (over 5’ 8”) might have to bend in certain parts of the loft.

2–9 May

£154 per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Stratford holiday 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 holiday rentals in Stratford

Superhost

Flat in Bridgeport

5.0 out of 5 average rating, 5 reviews

Ricport Studio 5

26 May – 2 Jun

£116 per night

Guest favourite

Guest suite in Milford

5.0 out of 5 average rating, 13 reviews

Modern Studio & Gamers Paradise Near Downtown

1–8 Aug

£156 per night

Superhost

Flat in Bridgeport

4.84 out of 5 average rating, 38 reviews

Lovely 1 bedroom cozy modern apartment w/75” 4K TV

29 Jul – 5 Aug

£110 per night

Superhost

Home in Stratford

4.83 out of 5 average rating, 12 reviews

The Rose

15–22 Mar

£153 per night

Guest favourite

Flat in Milford

5.0 out of 5 average rating, 48 reviews

The Pond Mill Retreat w/ 2 Bdrms & Pool

11–18 Sept

£155 per night

Guest favourite

Flat in Bridgeport

5.0 out of 5 average rating, 6 reviews

Beautiful Apartment Quiet Area

21–28 Apr

£116 per night

Guest favourite

Tiny home in Milford

4.96 out of 5 average rating, 53 reviews

Beach Cabana

13–20 Oct

£145 per night

Guest favourite

Flat in Fairfield

4.95 out of 5 average rating, 62 reviews

Sunny Fairfield Studio Apartment

14–21 Aug

£145 per night

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Quick stats about holiday 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

Holiday rentals in Stratford

Top-rated holiday rentals in Stratford

Guest suite in Fairfield

Flat in Milford

Guest suite in Fairfield

Flat in Milford

Loft in Milford

Home in Milford

Cottage in Easton

Guest house in Milford

Cottage in Milford

Home in Stratford

Flat in Brookfield

Loft in Bridgeport

Holiday rentals for every style

Houses

Flats

Hotels

Popular amenities for Stratford holiday rentals

Stay near Stratford's top sights

Other great holiday rentals in Stratford

Flat in Bridgeport

Guest suite in Milford

Flat in Bridgeport

Home in Stratford

Flat in Milford

Flat in Bridgeport

Tiny home in Milford

Flat in Fairfield

Quick stats about holiday rentals in Stratford

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Destinations to explore