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House holiday rentals in Bridgeport

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Top-rated house rentals in Bridgeport

Guests agree: These houses are highly rated for location, cleanliness and more.

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Home in Woodmont

4.92 out of 5 average rating, 26 reviews

Light-filled Beach House Steps from the Sand

Located in prime Bayview Beach, a one min stroll to the sandiest beach in Milford. Two floors with private patio. Main level: half-bath, Cooks kitchen with a 6 person dining area, living room with flatscreen. Upstairs: master w/king size bed & en-suite bath, kids bedroom w/ bunkbed, another full bath w/ tub. 3rd bedroom with queen bed and trundle twin. If you want a get-a-way from the city, or just an escape then come to this tucked-away home. Enjoy all that this coastline gem has to offer.

Guest favourite

Home in Fairfield

5 out of 5 average rating, 8 reviews

Newly built twin beach house within steps to beach

Keep it simple at this peaceful and centrally-located home. Newly built in 2019! Premier beach living at its finest. Steps to Fairfield’s beaches and less than a mile to downtown restaurants, shops, and bars. Fenced backyard. Central air throughout. Decks off the front and back with a Weber grill. Furnished with luxury furniture, sheets, comforters, and pillows. Smart TVs in every bedroom and living room. Tesla charging station at the house. Identical home next door available for larger bookings

Guest favourite

Home in Milford

4.96 out of 5 average rating, 24 reviews

*The W- close to beach, hiking, pizza, wineries*

-A brief walk to WIldemere (3 minutes) or Walnut Beach (10 minutes) to enjoy the sun and water. -7 minute walk to the new Tyde at Walnut Beach!!! This peaceful beach community is welcoming and ready for you to explore. Take a stroll to the coffee shop, restaurants, beach boardwalk, and the BEST ice cream shop-Walnut Beach Creamery. Maybe cook or order in to relax on the beautiful patio by the fire pit while the kids have s’mores! -quick drive to famous pizza and hiking and farms -train to NYC

Guest favourite

Home in Milford

4.92 out of 5 average rating, 78 reviews

Charming one bedroom house in Milford, CT

Charming, stylish, newly remodeling little house / centrally located, just minutes away from shopping, restaurants, beaches, train station and downtown. Great for travelers, just blocks away from I-95 and the Merritt Parkway. Short Walk: McDonald’s, Wendy’s, CVS, Walgreens, Big Y World Class Market, Stop & Shop Under 5 min drive: Silver Sands Park, Walnut Beach, train station, Downtown, restaurants Under 20 min drive: Costco, Wholefoods, Trader Joe’s, Connecticut Post Mall, Yale, Hospitals

Guest favourite

Home in Roxbury

5 out of 5 average rating, 10 reviews

Zoom In Map To 5*Roxbury "Painter Hill" PoshPadsCT

PoshPadsCT - Private 4-5-Bedroom hilltop retreat on a serene brook - a perfect getaway. New Hot Tub, Terrace, Trampoline. Located on a 3 acre property near historic estates, Maple Bank farm stand and Toplands Farm and just 1.5 hours from NYC. The house features beautiful fields, views, a large terrace with a gas grill, a firepit. Nearby hiking trails & Washington restaurants, shopping, distilleries, vineyards, breweries, and more! Ski Mohawk Mountain or Swim Lake Waramaug State Beach.

Guest favourite

Home in Northport

4.94 out of 5 average rating, 114 reviews

Cool pad, Private Rms, Walk to village, Wtr view

Beautiful pad on a tranquil street and walkable neighborhood. 5-10 minute walk to the village and 2-minute walk to the cliffs overlooking the bay and sound. Water view from one bedroom, great outdoor yard - very private. Updated amenities, marble bathroom, cozy indoor living area and very comfortable beds. The rental space is private and is the entire first floor of the home. The home is a two-story duplex with a shared entrance and private locking doors to each space. Wonderful location.

Home in New Milford

4.88 out of 5 average rating, 188 reviews

Renovated, one level home in an excellent location

Guests are sure to enjoy a memorable time in this beautiful fully furnished 3 bedrooms and 2 bathroom house. The house has been recently renovated to maximize comfort and overall experience. Excellent location close to major stores, restaurants and at walking distance to Candlewood Lake and Candlewood Lake Point private beach. Highlights: Free WIFI, Roku TV with Youtube TV, towels & beach towels, bed linens, and a beautiful deck with dining table, propane grill, and patio furniture.

Guest favourite

Home in New Fairfield

4.92 out of 5 average rating, 111 reviews

Beautiful Lakefront Retreat with Private Dock

Relax on the lake at this beautiful, one of a kind 3 bedroom, 2.5 bath DIRECT waterfront home in a private community on peaceful Squantz Pond, adjacent to Candlewood Lake. Enjoy spectacular views across the lake of unspoiled Pootatuck State Forest from the deck or screened in porch. Swim, fish, or just relax on the private dock. Kayak and paddleboard rental nearby. The home is central air-conditioned with a fully equipped kitchen. Our special place is waiting for you!

Home in Stamford

4.84 out of 5 average rating, 146 reviews

Gem by the water+ firepit and all fenced backyard

Take it easy at this unique and tranquil getaway. One block away from the water and three blocks away from Dolphin Cove. Enjoy walkings and site-seeings. Perfect for going kayaking, paddle boarding or just stay relaxing in the backyard. It is located at 5 minutes walking distance from the train station and 7 minutes away from downtown. Bus stop in front of the house. The house has a lower level that mostly is occupied by the host and sometimes with guests.

Guest favourite

Home in Milford

4.91 out of 5 average rating, 43 reviews

The Seashell House

Adorable bright and airy beach cottage steps to the sand with a great back yard . Original 1905 charming cottage with modern amenities . Direct beach access . Plenty of sleeping spots / trundles under built in beds . Outdoor shower and firepit . Come and enjoy Milford’s best beach with your family or friends . Milford not only has gorgeous beaches but also amazing restaurants and summer nightlife . Off season is perfect for travel nurses

Guest favourite

Home in Milford

5 out of 5 average rating, 100 reviews

Steps2Beach, Fish Pond w/Tropical Backyard Oasis!

🌟 Special Discounts on Early Birds, Last-Minute Stays & 7+ Nights! 🌴Steps from Walnut Beach & Silver Sands State Park, this guest-favorite escape offers a tropical backyard oasis with a cascading fish pond, multiple lounges, & a seasonal palm tree. Inside, relax in luxury with a gourmet kitchen, elegant furnishings, & modern amenities. Just 90 minutes from NYC, it’s the perfect retreat for beach days, nature adventures, & coastal charm!

Guest favourite

Home in New Milford

4.97 out of 5 average rating, 29 reviews

Serene Country home 24 mi Mohawk ski area

THIS IS A PRIVATE HOME🏡 THE BOTTOM FLR 2 car garage and a double bedroom with a full bathroom attached. THE MIDDLE FLR KITCHEN, LIVING, DINING 1/2 bath, wrap-around decks w/ a fire pit THE TOP FLR 1 K rm w/ a fireplace & a private deck 1 Q rm 1 ba w/ jet tub & standing shower 6 acres Foothills of the Berkshires May-Sept We provide day passes for access to tennis, pickle ball, pool, yoga, swim, water aerobics

Holiday rentals for every style

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Apartments

Convenient locations with everyday essentials

Hotels

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Spaces that are more than just a place to sleep

Popular amenities for Bridgeport house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home in Woodbury

4.94 out of 5 average rating, 18 reviews

Beautiful Litchfield - 2 homes in one

Guest favourite

Home in Stormville

4.94 out of 5 average rating, 178 reviews

Private Hudson Valley Country Retreat

Guest favourite

Home in Ridgefield

4.95 out of 5 average rating, 40 reviews

Modern, Charming New England Pool Home Getaway

Guest favourite

Home in Stony Brook

4.93 out of 5 average rating, 515 reviews

Spacious Studio Apartment- near SBU

Guest favourite

Home in Cheshire

5 out of 5 average rating, 131 reviews

Pool House

Guest favourite

Home in Monroe

4.96 out of 5 average rating, 199 reviews

Garden Level Suite with Beautiful Pool

Guest favourite

Home in Stamford

4.95 out of 5 average rating, 244 reviews

Midcentury Modern ZenHouse Sculptor Studio

Home in Danbury

4.86 out of 5 average rating, 112 reviews

Private apartment

Weekly house rentals

Guest favourite

Home in Pawling

5 out of 5 average rating, 221 reviews

Hobbit House of Pawling

Guest favourite

Home in New Milford

4.99 out of 5 average rating, 80 reviews

Candlewood Lake Family Waterfront Retreat

Home in White Plains

4.88 out of 5 average rating, 8 reviews

Indigo Inn III -A Retro Modern Cove White Plains

Guest favourite

Home in Pound Ridge

4.88 out of 5 average rating, 43 reviews

1840Farmhouse, 65"OLED4k, firepit, 3x4ktvs, 3acres

Guest favourite

Home in Shippan Point

4.94 out of 5 average rating, 114 reviews

OCEAN COAST LUXURY BEACH HOUSE/45 min to NYC

Guest favourite

Home in Waccabuc

4.98 out of 5 average rating, 57 reviews

Modern Lakefront Home in Hudson Valley

Guest favourite

Home in Madison

4.87 out of 5 average rating, 23 reviews

Historic Beachside Glamour

Guest favourite

Home in White Plains

4.86 out of 5 average rating, 189 reviews

Bright&Comfy 2bed/1ba in quiet duplex

Private house rentals

Home in Trumbull

4.87 out of 5 average rating, 38 reviews

Beautiful House to relax with the Family.

Guest favourite

Home in Wading River

4.96 out of 5 average rating, 494 reviews

Your Zen Retreat

Guest favourite

Home in East Haven

4.89 out of 5 average rating, 98 reviews

Welcome To Piper's Rest

Guest favourite

Home in Bedford

5 out of 5 average rating, 26 reviews

The Waterside Home - Pool, Tennis, Sauna & Golf

Guest favourite

Home in North Salem

4.93 out of 5 average rating, 30 reviews

North Salem Home with Pool & Great Yard

Guest favourite

Home in Carmel Hamlet

4.93 out of 5 average rating, 73 reviews

Country getaway with hot tub on 9 acres

Guest favourite

Home in Woodmont

4.98 out of 5 average rating, 43 reviews

Beachfront paradise- come, stay, relax!

Home in Ridgefield

4.79 out of 5 average rating, 19 reviews

Log House, sits on 3acres. A retired mini farm.

Quick stats about house rentals in Bridgeport

Total rentals
150 properties
Total number of reviews
2.4K reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
90 properties have a dedicated workspace

Destinations to explore