Waterfront holiday rentals in Stratford

4.92 out of 5 average rating, 190 reviews

Home in Carmel Hamlet

Lux Bungalow on the Lake

Beautiful, light flooded, waterfront home 1 hour from New York City. The 2 bedroom home is on picturesque Lake Carmel. Wake up, eat, sleep and relax to the tranquil view of the glistening water - truly an oasis! Take in a sunset while eating a meal at home, explore the shops and restaurants in a cute nearby town, take a walk around the lake, read a book by the cozy fireplace, hike, cook, kayak, ski, or just sit and enjoy. Centrally located close to Hudson Valley, Westchester and Connecticut.

4.97 out of 5 average rating, 578 reviews

Flat in Woodmont

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!

4.98 out of 5 average rating, 104 reviews

Flat in Milford

The Pond Mill Retreat w/ 2 Bdrms & Pool

Catch up on a little work or simply unwind. Everything is waiting for you in this cozy, yet functional space surrounded by a beautiful wooded area with pond. Your private entrance accommodations include a finished, walk-out lower-level apartment (~730 sq ft) containing thoughtfully appointed bedrooms, living room, kitchen, and full bathroom. Experience solitude while enjoying the convenience to Rt 15, I-95, & Boston Post Rd destinations. And if you require assistance, we live right upstairs.

4.92 out of 5 average rating, 206 reviews

Guest house in Milford

Chic Coastal Retreat: Modern Apt Steps from Beach

Enjoy our freshly renovated 2-bedroom apartment with a private entrance, kitchen, and in-unit washer/dryer all just a stone's throw from the beach. At Silver Sands State Park, take in views of Charles Island, accessible via a sandbar at low tide. Explore scenic bike trails or stroll the picturesque boardwalk. Perfect for families and group get togethers. Beach amenities are provided, including kayaks, and enjoy a private backyard where you can fire up the BBQ and fire pit. No pets, please.

4.94 out of 5 average rating, 144 reviews

Loft in Woodmont

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.

4.95 out of 5 average rating, 103 reviews

Cottage in Milford

SILVER SANDS BEACH COTTAGE MILFORD NEAR YALE/TRAIN

Classic 1920s beach cottage perfect for your summer at the shore! It is tucked away on a quiet street, across from Silver Sands Beach Milford. This cozy cottage offers 2 bedrooms with bonus loft sleeping area. In one of CT's most desired shoreline locations, steps to the private beach & Silver Sands State Park boardwalk, walnut beach, ice cream and cafe. Close to downtown green which offers bars and restaurants, train to NYC and New Haven, Yacht Clubs and Yale. Beach Vacation. Pet Friendly!

4.99 out of 5 average rating, 301 reviews

Home in New Haven

Q River House - 2 bdrm, minutes from Yale/Downtown

Q River House: newly remodeled two bedroom home in the historic Fair Haven neighborhood, conveniently located minutes from downtown New Haven and Yale. Take in river views with your morning coffee on the front porch and relax on the large and private back deck. Enjoy one of the city’s many fine restaurants or cook for yourself in the fully appointed modern kitchen. This riverfront home has been lovingly decorated with attention to style and comfort, and features off-street driveway parking.

4.96 out of 5 average rating, 224 reviews

Home in Milford

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!

4.95 out of 5 average rating, 117 reviews

Home in Southington

Connecticut Chalet - Private Pond, Firepit, Views!

Escape to a unique & stylish home perfectly tucked away in a picturesque New England town. Indulge in the privacy & serenity of this 5 acre wooded property and peaceful pond while being minutes from an abundance of restaurants, shops & entertainment. Enjoy the natural setting from the comfort of the glass enclosed sunroom with panoramic views of the property. This 3 bed, 2 bath home maintains it’s original 1960’s charm while boasting thoughtful modern touches and intentional functionality.

4.98 out of 5 average rating, 174 reviews

Home in New Haven

WaterviewsTakeWedding pics,CollegeTours Yale&Beach

Spectacular unobstructed Long Island Sound views to enjoy year-round out your front door along Pardee Seawall! This exceptional shore line property offers all new furniture & amenities. Minutes from wedding venues-perfect for getting dressed on your wedding day & taking photos literally right outside your door (props available). Near: Tweed NH Airport, beach, Yale University & Hosp, restaurants & museums. All new furniture, linens/towels, grill, fire pit, centralAC, WIFI. Onsite parking.

5 out of 5 average rating, 107 reviews

Cottage in South Salem

Oscaleta Guest House: Lakefront Cabin

Escapology-A spectacular lakeside destination, designed as a luxury suite with its own dock. Close to NYC and ideal for a quick trip, remote work or an extended retreat. Glamping-A cabin in the woods on a lake surrounded by nature, but tech-enabled with all the modern perks. Artfully Designed Space-Modern retrofit thoughtfully curated with custom artwork throughout this historic 1920's cottage. Purpose built for your outdoor routine- from grill to canoe…. We recommend 3+nights if you can.

4.97 out of 5 average rating, 143 reviews

Cottage in Weston

The River Loft

Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

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Popular amenities for waterfront rentals in Stratford

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

4.95 out of 5 average rating, 21 reviews

Flat in Branford

Stony Crk Studio ideal for trvl nurses…

CarolRating, 5 stars4 months ago

Great stay in Stony Creek Village with a view of Long Island Sound and short walk to the pier, Stony Creek Market (breakfast & lunch). I used the Library and went to services at the Stony Creek Congregational Church. Overall, a nice experience.

4.9 out of 5 average rating, 10 reviews

Flat in Milford

Kicking off Summer, on the beach in Milford, CT!

MarkRating, 5 stars5 months ago

Great place; wonderful 2 bed place, clean, cosy and top end, one of the nicer places I've stayed. Alison was super easy to communicate with and the location was great for a Christmas break. Was very happy with everything!

4.99 out of 5 average rating, 147 reviews

Flat in Northport

Amazing one bdrm flat at the beach!

BethRating, 5 stars2 weeks ago

Jeannette was there to greet us and made sure we knew where everything was and that we had everything we needed. She even provided breakfast. Her place was immaculate. The location was amazing. She made our departure very easy. We are looking forward to staying there again. If you looking for a great place to stay, this is it.

5 out of 5 average rating, 63 reviews

Flat in Norwalk

Phoenix Engine #1

GrantRating, 5 stars4 weeks ago

Nathan’s a great host and he provided a great welcome pack. Great home for my wife and I and adult son. Plenty of space and walkable to coffee shops and river. Awesome communication and offered a very helpful relaxed late check out at no cost. Totally recommend this host and this property

4.96 out of 5 average rating, 84 reviews

Flat in Guilford

Cozy Private Lake Q Retreat

JenniferRating, 5 stars3 weeks ago

Great little spot. This rental has everything you need. Forget something-they got it. Very clean and modern with thoughtful touches. Had an extended stay here and extended for longer. 1 bedroom with loft that owner made into another bedroom for me. Loved it. Great deck, stunning lake view from all the windows. Owner very responsive to any needs. 100 percent recommend. Neighborhood lovely and quiet. Amazing respite.

5 out of 5 average rating, 78 reviews

Flat in Fairfield

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

JenniferRating, 5 stars1 week ago

I had an excellent stay! Andy is responsive and accommodating. The space is lovely and as described , clean, and comfortable, tastefully decorated and stocked with starters needed for an easy stay, …. Example, dish soap, salt, pepper, bathroom supplies.

4.8 out of 5 average rating, 113 reviews

Flat in Stamford

Harborview/pool/freeparking/downtown

VontresseRating, 5 stars1 week ago

Ana was a great host, firstly the apartment smelled AMAZING and it was nice and cool, she had toiletries laid out and the bed was comfortable. The ambiance of the apartment was very welcoming and homey. Will definitely be back, thank you for the hosting.

4.92 out of 5 average rating, 121 reviews

Flat in Middlebury

Cozy Apartment with Water View of Brook

EvelindaRating, 5 stars2 weeks ago

We were recently in town to visit family, staying at Traci’s made our visit enjoyable and relaxing. Check-in was easy, the apartment was clean with a comfortable bed and a peaceful view of the brook. Overall, we had a pleasant stay, thank you Traci!

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Waterfront house rentals

4.83 out of 5 average rating, 100 reviews

Home in Milford

Beachfront house on Long Island Sound

JeffRating, 5 stars2 days ago

Great place, host and great location.

4.92 out of 5 average rating, 25 reviews

Home in Woodmont

Beachfront getaway in Milford

AllisonRating, 5 stars10 months ago

My husband and I stayed here with my mom, 3 yr old, and infant and had a lovely time. The house had everything we needed and nothing we didn’t need. This place was no frills but right on the water, and the price reflects that. Stairs are a bit on the steeper side so just be aware of that if you have anyone with bad knees or children learning to use stairs still. Our host was wonderful and very responsive, we liked him a lot! The beach out front is a bit rocky, so water shoes are a must. But it is so beautiful and peaceful! Our favorite thing was going out during low tide with the kids, you can walk really far out and we saw lots of horseshoe crabs and it was so much fun.

4.83 out of 5 average rating, 42 reviews

Home in West Haven

The Seabreeze

JulieRating, 5 stars6 months ago

Beautiful sunrise/sunset from living room. Very quiet. Joann very responsive.

4.8 out of 5 average rating, 330 reviews

Home in Port Jefferson

The Hilltop Harborview

DarrellRating, 5 stars2 weeks ago

Very quiet and peaceful.

4.96 out of 5 average rating, 100 reviews

Home in East Haven

Cozy Beach - Direct Waterfront!

SarahRating, 5 stars6 months ago

This house is a gem! I came to stay a week in off season with my dog, Rollo. The location is breathtaking, right on the Long Island Sound. We had a great time exploring the beach, looking for all the biodiversity in the birds and sea creatures, watching the boats, and this place is relatively close to an airport so watching the planes land and take off was awsome as well. We came for privacy, and I expected the beach to be a little more private than it was due to my dog's reactivity. But the neighbors did not seem to have issues with us, and once you are close to the water, especially in low tide, the beach is pretty open for all the locals. Walking around, the locals all waved and said hello. Not too many restaurants close by, but the Lobster Shack down the road had good food! Would stay again! The deck alone was worth it!

4.94 out of 5 average rating, 182 reviews

Home in Stormville

Private Hudson Valley Country Retreat

JackieRating, 5 stars2 weeks ago

This beautiful property has a special place in our hearts. We stayed in the A frame during COVID and we always wanted to come back. This time we stayed in the main house and it was phenomenal. Wish the weather was better for us to use the pool, but next time! It well worth the price. Only an hr from the city and it feels like a full vacation. Wonderful way to lose time time for a few days. We will be back!

4.97 out of 5 average rating, 92 reviews

Home in Black Rock

Cape on the Water

AlexRating, 5 stars2 weeks ago

Jim’s place was perfect for our stay. The house was exactly as advertised. Our favorite part was the beautiful view of the salt marsh in back with lots of birds to watch.