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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

Home in Ossining

4.85 out of 5 average rating, 137 reviews

Lower Hudson Valley Idyllic Retreat

Located 2 minutes from Teatown Nature Reserve (35 mins from NYC) on 1+ acre in the Lower Hudson Valley, this updated 2,600sf oasis is the perfect forest setting for your family or business retreat. It features an oversized gourmet chef's kitchen with adjoining dining room. There are 4 bedrooms, including a nursery/crib, additional sleeping spots, and stunning views from a perfectly perched solarium. The great room features a spectacular working fire place and floor to cathedral ceiling windows.

Guest favourite

Home in Milford

4.96 out of 5 average rating, 23 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 Clinton

4.94 out of 5 average rating, 127 reviews

Amazing 2BR Riverfront Gem

Unwind at this happy getaway, with an amazing river view, in a peaceful neighborhood, and in the heart of fall foliage and holiday scenes. The well-equipped kitchen overlooking the river is a pleasure for any cook. You will love to see our fairy-lit lawn, wishing well, chimenea, and charming décor. Only minutes to beaches, groceries, coffee shops, hiking trails and amazing CT scenery at every turn! Other favorites include Chamard Vineyard, Shopping Outlets, fantastic Restaurants, and lots more.

Guest favourite

Home in Roxbury

5 out of 5 average rating, 10 reviews

Zoom In Map Best 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 Morris

4.86 out of 5 average rating, 148 reviews

Bantam Lake Waterfront Retreat with Private Beach

Waterfront home on Bantam Lake, 3BR/2BA. Relax on the deck, enjoy the sunrise, swim at your private beach. Kayaks available for use (4); bring your boat or jet ski. Minutes away from hiking, snow skiing, vineyards, biking, and so much more. The area offers great restaurants and family friendly activities that are minutes away. BBQ on the gas grill, enjoy the fire pit on the beach. House is great for couples, individuals & families. Please check first if you plan to bring a boat. 7 maximum.

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, 182 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

4.93 out of 5 average rating, 107 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 Darien

4.8 out of 5 average rating, 182 reviews

Convenient and Cozy Antique Cape

Adorable little house in Darien CT, with a fireplace in winter and the beautiful local beaches in the summer. Right across from Trader Joe’s and around the corner from route 1 and Interstate 95, the little house is super convenient to local amenities. Probably the best perk of its central location is that it’s nestled behind Rorys, the best pub ever, so there’s no need to even cook if you are too busy or just don’t want to after working all day or a long day at the beach

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

Holiday rentals for every style

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Apartments

Convenient locations with everyday essentials

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Stylish accommodation and amenities

Popular amenities for Bridgeport house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home in Stormville

4.94 out of 5 average rating, 176 reviews

Private Hudson Valley Country Retreat

Guest favourite

Home in North Salem

4.99 out of 5 average rating, 220 reviews

Converted Barn House

Guest favourite

Home in Cheshire

5 out of 5 average rating, 128 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 Litchfield

4.99 out of 5 average rating, 79 reviews

Hilltop House w/POOL/SPA- HOST & Co.

Guest favourite

Home in Stamford

4.95 out of 5 average rating, 240 reviews

Midcentury Modern ZenHouse Sculptor Studio

Home in Lagrangeville

4.84 out of 5 average rating, 133 reviews

Classic Hudson Valley Farmhouse Nestled in 9 Rolling Acres

Home in Fairfield

4.71 out of 5 average rating, 7 reviews

Modern Beach Area Vacation Home With Pool

Weekly house rentals

Home in Fairfield

4.86 out of 5 average rating, 76 reviews

Bright 3-bedroom house with ample parking & patio!

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

4.89 out of 5 average rating, 36 reviews

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

Guest favourite

Home in Waccabuc

4.98 out of 5 average rating, 57 reviews

Modern Lakefront Home in Hudson Valley

Guest favourite

Home in Branford

4.9 out of 5 average rating, 50 reviews

Spacious Modern Beach House

Guest favourite

Home in Cos Cob

5 out of 5 average rating, 14 reviews

GREENWICH HOUSE WITH NYC FLAIR/CLOSE TO BEACH /NYC

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, 180 reviews

Bright&Comfy 2bed/1ba in quiet duplex

Private house rentals

Home in Trumbull

4.86 out of 5 average rating, 37 reviews

Beautiful House to relax with the Family.

Home in Norwalk

4.78 out of 5 average rating, 23 reviews

Hollow Spring Retreat

Guest favourite

Home in Wading River

4.96 out of 5 average rating, 488 reviews

Your Zen Retreat

Guest favourite

Home in Pawling

5 out of 5 average rating, 212 reviews

Hobbit House of Pawling

Guest favourite

Home in Bedford

5 out of 5 average rating, 25 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, 70 reviews

Country getaway with hot tub on 9 acres

Guest favourite

Home in Woodmont

4.98 out of 5 average rating, 42 reviews

Beachfront paradise- come, stay, relax!

Quick stats about house rentals in Bridgeport

Total rentals
150 properties
Total number of reviews
2.6K reviews
Family-friendly rentals
80 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