Vacation rentals in Stratford

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Top-rated vacation rentals in Stratford

Guests agree: these stays are highly rated for location, cleanliness, and more.

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.

Oct 24 – 31

$99 per night
Guest favorite

Apartment in Milford

4.94 out of 5 average rating, 104 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!

Jun 10 – 17

$181 per night
Guest favorite

Guest suite in Fairfield

4.93 out of 5 average rating, 107 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.

Aug 18 – 25

$107 per night

Popular amenities for Stratford vacation rentals

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

4.93 out of 5 average rating, 92 reviews

Lovely water front lower-level loft, free parking

Aug 14 – 21

$110 per night
Guest favorite

Apartment in Milford

5.0 out of 5 average rating, 46 reviews

The Pond Mill Retreat w/ 2 Bdrms & Pool

Sep 11 – 18

$136 per night
Superhost

Home in Stratford

4.83 out of 5 average rating, 12 reviews

The Rose

Feb 28 – Mar 7

$131 per night
Superhost

Home in Fairfield

4.9 out of 5 average rating, 31 reviews

Fairfield 2nd FL Suite w Private Entry & Parking

Sep 7 – 14

$93 per night
Guest favorite

Home in Fairfield

4.91 out of 5 average rating, 65 reviews

Fairfield 2nd FL Suite w Private Entry & Parking

May 7 – 14

$98 per night
Guest favorite

Home in Stratford

5.0 out of 5 average rating, 10 reviews

Lordship Beach House - Pool & Beach (seasonal)

Sep 26 – Oct 3

$595 per night
Guest favorite

Cabin in Trumbull

4.98 out of 5 average rating, 42 reviews

Rustic cabin with spectacular lake view

Dec 9 – 16

$141 per night
Guest favorite

Tiny home in Milford

4.96 out of 5 average rating, 49 reviews

Beach Cabana

Sep 12 – 19

$150 per night
Guest favorite

Guest suite in Wilton

5.0 out of 5 average rating, 22 reviews

Guest suite with private enter

Apr 30 – May 7

$82 per night
Guest favorite

Apartment in Fairfield

5.0 out of 5 average rating, 50 reviews

Bright, private 1,000 sq. ft. 1-Bedroom Apartment

Sep 29 – Oct 6

$120 per night
Guest favorite

Home in Milford

5.0 out of 5 average rating, 23 reviews

Luxury Beach Oasis with Amazing Ocean Views

May 11 – 18

$558 per night
Guest favorite

Cottage in Milford

4.99 out of 5 average rating, 72 reviews

Modern Farmhouse Style Cottage 3BR Walk To Beach

Oct 27 – Nov 3

$322 per night

Quick stats about vacation rentals in Stratford

Total rentals

160 properties

Rentals with dedicated workspaces

100 properties have a dedicated workspace

Rentals with a pool

10 properties have a pool

Pet-friendly rentals

40 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 190 vacation rentals in Lordship, over 190 vacation rentals in Boston Ave - Mill Hill, and over 190 vacation rentals in Stratford Center Historic District.

  • 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 Apartment Rentals in Stratford?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with a kitchen, over 10 homes with free parking, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do house rentals in Stratford have free parking?

    Absolutely! We offer over 100 house 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 house rentals in Stratford have a kitchen?

    Absolutely! We offer over 90 house 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 cottage rentals in Stratford have wifi?

    Absolutely! We offer over 10 cottage 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 40 vacation rentals for guests traveling with pets.

Destinations to explore