
Places to stay near Jennings Beach
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Top-rated holiday rentals near Jennings Beach
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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.
4.97 out of 5 average rating, 113 reviews
1956 House of the Year Award. Easy commute to NYC.
Architectural masterpiece, designed by famous architect Ulrich Franzen. House of the year awarded in 1956 by Architectural Record, featured in LIFE and House and Garden magazines. Taste the unique experience of modernist living, surrounded by nature yet walking distance to the beautiful town of Rye, the beach, natural parks and 45m by train to NYC. The house is filled with light,all the rooms have forest views,you feel inmersed in nature while enjoying the magical experience of modernist living!
4.91 out of 5 average rating, 146 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.
4.94 out of 5 average rating, 145 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.
4.93 out of 5 average rating, 206 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.
4.88 out of 5 average rating, 109 reviews
Private Studio Apartment Kitchen Fully Furnished
This 625 sqft fully furnished studio apartment has its own private entrance and sleeps 2-3 with a queen bed and Murphy bed. Other than outside, there is no contact with other people (hosts, other guests, etc) possible unless the guest allows such. The unit consists of a living room, dining space (breakfast basics provided), kitchen, full bathroom/laundry. Walk to Fairfield U; an easy train ride to NYC. (Need the Murphy bed? PLEASE do not wait until just before checkin to let us know that!)
4.95 out of 5 average rating, 472 reviews
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!
4.97 out of 5 average rating, 270 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.
4.95 out of 5 average rating, 120 reviews
5 Minute Walk to Beach & Downtown Fairfield
This Immaculate 3-bedroom cape in the desirable Fairfield Beach Area is only a 5 minute walk to the sand. The home has just been beautifully updated and has all modern amenities. Lovely level fenced in backyard and enjoy an evening cocktail on the deck. Close enough to the train and downtown to walk and take a stroll to the Marina in the evening. The location is just perfect and the house is a wonderful place to relax and recharge.
4.97 out of 5 average rating, 105 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.
4.96 out of 5 average rating, 355 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.
4.98 out of 5 average rating, 195 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.
4.96 out of 5 average rating, 232 reviewsPopular amenities for holiday rentals near Jennings Beach
Apartment rentals with wifi

Cozy 3-Bed 2-Bath Condo | Parking and Laundry!
4.84 out of 5 average rating, 161 reviews
Downtown gem w/ parking, Wi-Fi+!
4.84 out of 5 average rating, 109 reviews
Stunning, Spacious, Spotless. Close to Yale.
4.84 out of 5 average rating, 303 reviews
Comfortable apartment near all communal facilities
4.93 out of 5 average rating, 56 reviews
Norwalk Loft with Private Patio
4.9 out of 5 average rating, 21 reviews
1856 Trading House close to water
4.96 out of 5 average rating, 46 reviews
Coastal Holiday Getaway - Waterfront Rowayton
5.0 out of 5 average rating, 17 reviews
Artist Apartment in the Heart of Downtown Stamford
4.78 out of 5 average rating, 50 reviewsFamily-friendly house rentals

3 Bedroom Beach House with Hot Tub!
4.97 out of 5 average rating, 158 reviews
Peaceful Light-Filled Guesthouse salt pool/sauna
5.0 out of 5 average rating, 190 reviews
Cozy Colonial - Private Hot Tub & Entire House
4.96 out of 5 average rating, 241 reviews
The ARLO - Walk to Brewery & Restaurants
4.99 out of 5 average rating, 193 reviews
Adorable Beach House on LI Sound
4.98 out of 5 average rating, 112 reviews
Fully renovated/Walk to water & shops/fenced yard!
4.98 out of 5 average rating, 161 reviews
The Cozy Little Cottage
4.97 out of 5 average rating, 155 reviews
Stareway to Heaven
5.0 out of 5 average rating, 62 reviewsApartment rentals with air conditioning

Spacious Westport Apt surrounded by nature!
4.92 out of 5 average rating, 340 reviews
2BDFairfield Work & Relax Space w. Patio+Fast WiFi
4.88 out of 5 average rating, 103 reviews
Water front studio apartment with fireplace.
4.97 out of 5 average rating, 650 reviews
Huckleberry Quarters, the Cozy Redding Retreat.
4.94 out of 5 average rating, 513 reviews
Spacious Studio with Pool Table
4.88 out of 5 average rating, 243 reviews
Stylish Sheek Loft Ricport Studio 2, Downtown
4.88 out of 5 average rating, 167 reviews
Luxurious 3BR Apartment w/ Parking & Gym
4.95 out of 5 average rating, 127 reviews
Amazing one bdrm flat at the beach!
4.99 out of 5 average rating, 162 reviewsOther great holiday rentals near Jennings Beach

The River Loft
4.97 out of 5 average rating, 246 reviews
1BR full cottage, 1 min walk to private beach
4.99 out of 5 average rating, 173 reviews
Summer Sale! CozyCottage/Pet-friendly/ WalktoBeach
4.94 out of 5 average rating, 419 reviews
Delightfully Renovated Colonial Barn by the Beach!
4.98 out of 5 average rating, 92 reviews
The Creekside Cottage
4.96 out of 5 average rating, 55 reviews
Enchanting Guest Cottage
4.96 out of 5 average rating, 26 reviews
Nama-stay: sweet Saugatuck Shores beach cottage
5.0 out of 5 average rating, 25 reviews
Fairfield’s Four bedroom Family Home
5.0 out of 5 average rating, 30 reviewsDestinations to explore
- Times Square
- Central Park Zoo
- Yale University
- Jones Beach
- Columbia University
- American Dream
- Yankee Stadium
- MetLife Stadium
- New York City Center
- Rockefeller Center
- United Nations Headquarters
- Bear Mountain State Park
- Empire State Building
- Bryant Park
- Barclays Center
- Citi Field
- Grand Central Terminal
- Cooper's Beach, Southampton
- Brooklyn Bridge
- Radio City Music Hall
- Astoria Park
- Fairfield Beach
- Thunder Ridge Ski Area
- Bronx Zoo





