Places to stay near Jennings Beach

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Top-rated holiday rentals near Jennings Beach

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

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Top guest favourite
The spacious living area features a large window allowing natural light to fill the room. A comfortable seating arrangement includes a plush armchair and a sofa, accompanied by a coffee table. Decorative plants and a decorative rug complement the elegant furnishings, including a classic wooden armoire.
Guest suite in Fairfield
4.96 out of 5 average rating, 270 reviews

2 BRm Suite; Ktchn; Livng area; wash/dryr; Private

Fully accessorized, large (919 sq ft) beautiful suburban space with bedroom (queen); convertible Murphy bed (queen), in-room sitting area/large screen TV, kitchenette; 2nd room: bedroom (queen) with living space / large screen TV; private full bath; in-suite washer/dryer; private entry to suite (front door; up 1 flight of stairs). Includes light continental breakfast. Owners on property. Off street parking. Train station a mile away (NYC: 70 min). 2 miles to beach. Easy walk to Fairfield U.

Top guest favourite
The kitchen features modern cabinetry with a contrasting dark granite island. Three cushioned stools are positioned at the island. Natural light enters through a window above the sink, illuminating new stainless steel appliances and a sleek backsplash. A door leads to the outdoor area.
Home in Black Rock
4.97 out of 5 average rating, 112 reviews

Cape on the Water

Welcome to our Cape on the Water! This unique property is located on beautiful Ash Creek, an inlet off Long Island Sound offering views of tidal wetlands, including tons of fish, bird, kayakers, paddle boarders, small sail boats etc. The house is a newly renovated Cape Cod with an open floor plan, updated Kitchen and bath rooms. Refinished oak hardwood floors through out the entire house. Large deck -great view. The house has a very cozy feel and has been also updated with brand new HVAC system.

Top guest favourite
The living area features a dark grey sofa adorned with decorative pillows, positioned on a textured area rug. A small wooden side table stands next to the sofa, and a framed landscape artwork hangs on the wall. A dining area is visible through the doorway.
Home in Fairfield
4.94 out of 5 average rating, 142 reviews

Downtown Fairfield 3 bedroom Colonial

Enjoy a charming, 3 bed/2 full bath Colonial that is only a 4 block walk from the coffee shops, bars, and restaurants on the Post Road and .7 mile from the Fairfield Train Station. The house is over 1500 sq. feet on a quiet street and only a mile to the town beaches. Work has taken me from Fairfield, but it remains home, so the house is fully stocked with everything. If you're into shooting hoops, you'll like the lined and paved court. Small well-trained dogs and longer stays are negotiable.

Guest favourite
A spacious bedroom features a king bed with a soft green duvet and decorative pillows. Two nightstands with lamps are positioned on either side. Natural light enters through two windows adorned with bamboo shades. A framed coastal artwork is displayed above the headboard.
Guest suite in Fairfield
4.93 out of 5 average rating, 204 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.

Guest favourite
A spacious deck offers a panoramic view of the beach and water, with sunlight reflecting off the surface. Colorful chairs are positioned for relaxation, while shadows created by the railing add depth to the scene. The sandy shore can be seen in the distance.
Cottage in Milford
4.88 out of 5 average rating, 109 reviews

Cheerful 3 Bedroom Cottage with Fire Place

We are happy to still offer some dates for September. Come enjoy the solitude of the beach as the tide ebbs & flows. Reconnect with loved ones in this family-friendly place. Enjoy strolls on the beach located just out the back door or a sunset meal on the back porch. This wonderful cottage offers everything you will need during your stay. Including, comfortable beds, beach strolls and a bright upgraded kitchen with many amenities. The 3 bedrooms will fit up to 8 people comfortably.

Top guest favourite
The studio features a neatly arranged sleeping area with a quilted bedspread in blue and white patterns. A desk with a chair is positioned nearby, allowing for a focused workspace. Natural light streams through sheer curtains, creating a bright and welcoming ambiance.
Home in Bridgeport
4.95 out of 5 average rating, 111 reviews

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.

Top guest favourite
Two wicker chairs with patterned cushions are positioned beside a large window, offering a panoramic view of the sandy beach and ocean. The serene landscape includes gentle waves and distant beachgoers, framed by a bright sky.
Home in Milford
4.99 out of 5 average rating, 159 reviews

Serene Waterfront Retreat - 400 ft Private Beach!

Welcome to a slice of waterfront heaven! Located on Milford's Cedar Beach, this newly renovated 3 bedroom / 1.5 bath home features over 400 feet of private beach. Enjoy breakfast prepared in the Chef's kitchen while watching one of the most radiant sunrises you will ever see. Stunning views from every room in the house. Wade into Long Island Sound with your own private beach. Located 3 doors down from the CT Audubon Society, known for its views & wildlife. We can't wait to host you!

Top guest favourite
A modern, two-story structure showcases large windows framed by climbing greenery. A stone pathway leads to a glass-paneled door, with potted flowers positioned along the entrance. The surrounding area is filled with trees, creating a serene atmosphere.
Cottage in Weston
4.97 out of 5 average rating, 241 reviews

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

Superhost
A well-appointed bedroom features a spacious bed with decorative pillows, complemented by a cozy armchair with a vibrant red cushion. Natural light fills the room through large windows adorned with blinds, while an elegant painting adorns the wall above the bed.
Apartment in Fairfield
4.84 out of 5 average rating, 161 reviews

Cozy 3-Bed 2-Bath Condo | Parking and Laundry!

Come stay in our clean and cozy condo located close to Fairfield University, great restaurants, local grocery stores, appliance centers, and other essential shops. Also includes: - Free Wi-Fi - Washer and dryer - Keurig with K-cups - Full kitchen with essentials - Smart Roku TVs with apps (Netflix, Hulu, etc.) - Fenced in/gated backyard - Outdoor patio set and grill - Free parking (4 car max) - Central heating and AC Perfect for those that need a temporary space!

Top guest favourite
A rustic barn-style home features a wooden exterior with multiple large windows, enhancing natural light. A spacious elevated deck is surrounded by lush greenery, while an outdoor umbrella offers shade. The setting is serene, with a glimpse of the nearby brook and wooded area.
Home in Fairfield
4.96 out of 5 average rating, 354 reviews

Beautifully Restored Barn With New England Charm

Set back from the road on one wooded acre with a brook, this renovated 4-bedroom converted barn pairs rustic New England character with modern comfort. Expect 30-foot ceilings, exposed beams, oversized windows, a babbling brook, large yard, eclectic art and furniture, a grand piano, a stocked kitchen, deck, grill, and space to gather. A memorable Fairfield stay for families, couples, small groups, beach weekends, and quiet escapes.

Top guest favourite
The bedroom features a queen size spindle bed with quality bedding, flanked by two nightstands with lamps. A dedicated work desk is equipped with a lamp and USB ports. Shelving adds storage, while a small seating area is present, illuminated by natural light from the windows.
Flat in Fairfield
4.98 out of 5 average rating, 193 reviews

Sunny Fairfield Studio Apartment

Enjoy this sunny, newly-renovated, modern Fairfield studio apartment, located in the carriage building of a historic early 1900's house. Great for an individual, couple, or family. Well situated, a short drive to Sacred Heart & Fairfield Universities, downtown Fairfield and the beach, Silverman's Farm and other Easton farms for apple picking, petting zoos, and the like, and Fairfield Metro Station for a 1 hour train ride to NYC.

Top guest favourite
Home in Fairfield
4.96 out of 5 average rating, 228 reviews

Cozy Cottage with Fire Pit, near Beach

Escape to Fairfield Cottage, a stylish 3-bed, 2-bath retreat 90 mins from NYC. Comfortably sleeping 8, this sun-drenched home features a private patio with a fire pit, a fully equipped kitchen, and two fireplaces. Perfect for families and just 3 miles from the beach, it's your ideal getaway for relaxation and connection. Enjoy a dedicated workspace, fast Wi-Fi, and numerous family-friendly amenities.

Popular amenities for holiday rentals near Jennings Beach