
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.

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!

Cozy Winter Escape • Firepit • Near Train & I-95
*Inquiries welcome | longer stays 🍁 *Beautiful 3BR, 2BA home on the Housatonic River *Balcony w/ stunning water views * SHARED AMENITIES : driveway, yard, shed *Historic neighborhood near I-95 & Metro-North Railroad *20 min to Yale, UB, Fairfield U, & SHU *Near hospitals: Yale, BPT, ST. V’s *Perfect for groups & families * 1 hr to NYC *5 min drive to the beach *10 min drive to Hartford Healthcare Amphitheater & Webster Bank Arena *Lots of local breweries and restaurants to explore.

#37 - Luxury Collection
Escape to this serene modern farmhouse retreat along Far Mill River, perfect for couples or small families. Enjoy a minimalist aesthetic with designer furniture from CB2, Crate & Barrel, and more. The first floor boasts a gourmet kitchen, plush couch, and a deck with seating, grill, and fire pit. High-speed Wi-Fi and luxurious touches enhance comfort. Upstairs, the master suite features a king bed, a work area, and a balcony with stunning river views. Ideal for a romantic or peaceful getaway.

Charming Folk Victorian Home
This spacious and beautiful Folk Victorian style farmhouse was built in 1917. This home has been updated to include all the modern-day necessities but still has all the charm of a 100 plus year old home! This home is truly the best of the best when it comes to location on the Golden Coast. Whether you are here to visit Fairfield County, New Haven County, or even NYC, you will find this home is close to everything! We are minutes from I-95, Route 15, Route 8, and Metro North Train Station!

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.

New & Modern Studio Apartment in Fairfield
This newly reconstructed downstairs stylish, modern, and spacious studio features a queen bed & a queen pull-out sofabed with remote lighting, luxe bathroom with towels and refillables, a fully loaded sleek kitchen, a 70” TV with surround sound, and guest-controlled ambient lighting. Enjoy a private entrance, in-suite laundry, guest-controlled heat, and ceiling fan. Close to Fairfield & Sacred Heart Universities, shops, beach, and quick NYC transit. Comfort and convenience in one chic space!

The ARLO - Walk to Brewery & Restaurants
Newly remodeled and designed, The ARLO combines a seamless blend of luxury & comfort for your family. Walking distance to Dockside brewery & stand-out local restaurants, while only 1 mile from the beautiful Walnut Beach. Enjoy a thoughtful & comfortably designed living room, cook in the chef-style kitchen, indoor/outdoor living with a game room and fully-fenced yard. -Less than 2 minutes to The Tyde wedding venue. -15 min to Fairfield U & Sacred Heart -15 min to YALE -0.2 miles off I-95

Cozy Studio in Bridgeport
Charming and fully equipped studio located in the heart of Bridgeport. Perfect for business travelers, couples, or solo adventurers, this cozy retreat features a comfortable bed, high-speed Wi-Fi, a private entrance, and a fully stocked kitchen for your convenience. Enjoy easy access to local restaurants, cafes, and shops, as well as public transportation and major highways. Whether you’re here for work or leisure, this studio offers everything you need for a relaxing and stress-free stay

Urban Garden Suite
Relax & Recharge in Westville’s Hidden Gem in New Haven. Unwind in this serene, beautiful, cozy, spotless garden apartment tucked inside a historic three-family home in charming Westville. The cozy, open-concept design blends modern upgrades with warm, thoughtful touches, creating the perfect balance of comfort and style.🌿 Enjoy peaceful surroundings, inviting details, and everything you need for a seamless stay. Your attentive (yet discreet) hostess ensures you’ll feel truly at home.

New & Stylish 2 King Bed Apartment w/ Grand Dining
🌟 Modern 2BR Retreat – Renovated & Wheelchair Accessible 🏡 Welcome to your perfect stay! Our newly renovated 2BR apartment offers a stylish and comfortable space for families, business travelers 💼, and couples ❤️. Designed for accessibility, it features a wheelchair ramp for easy entry. Enjoy all the modern amenities you need, plus a prime location near great restaurants 🍽️, shopping 🛍️, and top attractions 🌍. Book now and experience a hassle-free, cozy getaway!

Newly renovated beach house!
Come relax at our newly renovated home just steps away from the beach! Featuring a fully fenced in back yard, beautiful outdoor shower, BBQ grill, & fire pit, this three bedroom home (including a bunk room) is the perfect beach vacation destination. Walk to the beach, restaurants, coffee house, ice cream parlor, deli, convenience store, liquor store, and more! Just steps to Tyde wedding venue or a short drive to Sacred Heart, Fairfield University & Yale.

Comfortable apartment near all communal facilities
I have an apartment located in an excellent quiet area with easy access. It is furnished and is very close to different areas such as supermarkets, restaurants, hospitals and universities. It also has 100% filtered water to drink. Something very important is that NO type of drugs are accepted, NO Viper or electronic cigarettes or Hookah are NOT accepted on this property. If we find odors or drug residues, they will be reported and fined.
Popular amenities for Stratford vacation rentals
Other great vacation rentals in Stratford

St Mary's by the Sea- in Black Rock

Cece's Nature Lover Resort

Room with great view

lakeside single private bedroom

Private Room | Shared Comfort 1

Comfy Stay Near by Yale & Hospital

Luxury Beach Guest Room - Yale, UNH, VA, Beach!

Modern Room 6 Minutes From Yale
When is the best time to visit Stratford?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$32,637 GYD | G$30,754 GYD | G$31,381 GYD | G$36,193 GYD | G$44,980 GYD | G$51,256 GYD | G$54,603 GYD | G$53,976 GYD | G$44,352 GYD | G$38,913 GYD | G$36,402 GYD | G$36,611 GYD |
| Avg. temp | 0°C | 1°C | 4°C | 10°C | 16°C | 21°C | 24°C | 24°C | 20°C | 14°C | 8°C | 3°C |
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 210 vacation rentals in Stratford Center Historic District, over 210 vacation rentals in Lordship, and over 210 vacation rentals in East End.
Do cottage rentals in Stratford have air conditioning?
Absolutely! We offer over 10 cottage 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 air conditioning, over 10 homes with a kitchen, over 10 homes with wifi, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do cottage rentals in Stratford have free parking?
Absolutely! We offer over 10 cottage 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 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 110 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 60 vacation rentals for guests traveling with pets.
Quick stats about vacation rentals in Stratford

Total vacation rentals
Explore 170 vacation rentals in Stratford

Nightly prices starting at
Stratford vacation rentals start at G$6,276 GYD per night before taxes and fees

Verified guest reviews
Over 5,880 verified reviews to help you choose

Family-friendly vacation rentals
110 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 60 rentals that welcome pets

Vacation rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
100 properties have a dedicated workspace

Wi-Fi availability
170 of Stratford vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Stratford rentals

4.8 Average rating
Stratford stays are highly rated by guests—averaging 4.8 out of 5!
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