
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.

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.

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.

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.

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.

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.

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.

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!

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

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!

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.

Ocean House
Rare opportunity to rent your own 100’ Private Beach Front Oasis and enjoy all four seasons! This one-of-a-kind gem on a full sandy acre is only 60 miles from NYC. Brand new chef's kitchen w. Viking appliances. Living room w. wall of glass showcasing the breathtaking views of the Sound. The home also has a hot sauna & in sauna shower. Port Jefferson ferry (5mins away) connects you to New England. Our prices are not negotiable.

Renovated Cape Near beach, with Fire Pit and BBQ
Beautifully renovated 3-bed, 2-bath home perfect for families or groups of up to 9. Features a cozy fireplace, fully equipped kitchen, dedicated workspace, and a patio with a fire pit & BBQ. Located in a quiet neighborhood minutes from Fairfield University and Fairfield beaches, this bright and inviting space is your ideal retreat. Enjoy modern amenities and a seamless self-check-in experience.
Popular amenities for holiday rentals near Jennings Beach
Apartment rentals with wifi

Downtown gem w/ parking, Wi-Fi+!

Stunning, Spacious, Spotless. Close to Yale.

Comfortable apartment near all communal facilities

1856 Trading House w/ walk to water

Norwalk Loft with Private Patio

Coastal Holiday Getaway - Waterfront Rowayton

Artist Apartment in the Heart of Downtown Stamford

Cozy private furnished apartment
Family-friendly house rentals

Oceanfront Beach House w/ Private Hot Tub

The Cozy Little Cottage

Adorable Beach House on LI Sound

Fully renovated/Walk to water & shops/fenced yard!

Peaceful Light-Filled Guesthouse salt pool/sauna

The ARLO - Walk to Brewery & Restaurants

1956 House of the Year Award. Easy commute to NYC.

5 Minute Walk to Beach & Downtown Fairfield
Apartment rentals with air conditioning

Sunny Fairfield Studio Apartment

Spacious Westport Apt surrounded by nature!

Water front studio apartment with fireplace.

Spacious Studio with Pool Table

Stylish Sheek Loft Ricport Studio 2, Downtown

Huckleberry Quarters, the Cozy Redding Retreat.

Luxurious 3BR Apartment w/ Parking & Gym

NORTHPORT APARTMENT: Private, Clean, Cozy
Other great holiday rentals near Jennings Beach

1BR full cottage, 1 min walk to private beach

Summer Sale! CozyCottage/Pet-friendly/ WalktoBeach

The Colonial Cottage at Fairfield Beach

The Creekside Cottage

Southport Shoreline Charm: Elegant Coastal Escape

Fairfield’s Four bedroom Family Home

Private house, Walk to Beach, Train, Town, Theatre

Enchanting Guest Cottage
Destinations to explore
- Times Square
- Central Park Zoo
- Yale University
- Jones Beach
- Columbia University
- Yankee Stadium
- American Dream
- MetLife Stadium
- New York City Center
- Rockefeller Center
- United Nations Headquarters
- Empire State Building
- Bear Mountain State Park
- Barclays Center
- Bryant Park
- Citi Field
- Grand Central Terminal
- Cooper's Beach, Southampton
- Brooklyn Bridge
- Radio City Music Hall
- Astoria Park
- Fairfield Beach
- Thunder Ridge Ski Area
- The Metropolitan Museum of Art





