Holiday rentals in Darien

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Top-rated holiday rentals in Darien

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

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Top guest favourite

Cottage in Cortlandt

4.99 out of 5 average rating, 190 reviews

The Little Cottage in the Woods

The Little Cottage in the Woods Nestled among the trees, and in close proximity to our main house, this studio cottage is newly refurbished, very private and is in a great location to access the Hudson Valley. Hiking trails are within minutes of the cottage or right out the front door. Golf courses are also minutes away. Whether you are in the area on business or just looking to escape for the weekend and enjoy the out doors. It is situated on 9 1/2 hikeable acres, all available to our guests

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Home in Poughkeepsie

4.76 out of 5 average rating, 126 reviews

Newly Renovated & Comfortable Home-Vassar/Marist

Leave the busy city and the hustle and bustle behind. Relax and rejuvenate yourself in the Hudson Valley. This retreat has all the amenities (fully equipped kitchen, spacious deck/backyard, fire pit, grill, and parking on premises available). Take a walk or bike ride at the Hudson Valley Rail Trail, hike at Mt. Beacon, explore Dutchess Wine Trail c/o Clinton Vineyards, shop at the Poughkeepsie Galleria, or relax at Hand and Stone Massage. There is so much for you, family and friends to do.

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Guest house in Milford

4.92 out of 5 average rating, 205 reviews

Chic Coastal Retreat: Modern Apt Steps from Beach

Enjoy our freshly renovated 2-bedroom apartment with a private entrance, kitchen, and in-unit washer/dryer all just a stone's throw from the beach. At Silver Sands State Park, take in views of Charles Island, accessible via a sandbar at low tide. Explore scenic bike trails or stroll the picturesque boardwalk. Perfect for families and group get togethers. Beach amenities are provided, including kayaks, and enjoy a private backyard where you can fire up the BBQ and fire pit. No pets, please.

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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.

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Home in West Haven

4.79 out of 5 average rating, 43 reviews

Beachside Retreat

***Brand new to Airbnb, the Beachside Retreat is perfect for a quick getaway or a longer short term stay. Gorgeously renovated home has 4 spacious bedrooms, living room & dining room large enough to entertain and kitchen perfect for making those home-away-from-home meals. Across the street from the beach, wake up to stunning sunrises with your morning coffee or relax on the wrap around porch and watch the sunset. With walking trails, restaurants and shops close by you never have to go far.

Top 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.

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Home in Baldwin

4.85 out of 5 average rating, 133 reviews

Clarissa's Paradise

RESERVE NOW: This ideally located five-bedroom totally renovated home is the perfect spot for a family fun vacation. Located within walking distance of the well known playground and spray ground. The home features a spacious patio, central air conditioning, baseboard heating, WiFi, and Cable tv. The open layout provides perfect gathering spaces for your family, and all bedrooms are spacious and comfortably appointed. 4 full bathrooms . Sleeps 10. PLEASE NO PARTIES ARE STRICKLY PROHIBITED

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Guest suite in Branford

4.9 out of 5 average rating, 99 reviews

Granite Bay Getaway - Private Studio Apartment

Enjoy Long Island Sound in this cozy getaway. Three block walk to shore. Quiet residential neighborhood. Private deck with lovely afternoon light. Private entrance. Fully equipped eat in kitchen. Picturesque shoreline town of Branford. Many wonderful restaurants, 2 within walking distance. Land trust hiking trails at end of street. Ten minutes to New Haven, Yale & Avelo airport. Train station 2 miles away with connections to New York City and Boston. ½ mile from CT Hospice.

Guest favourite

Home in Mastic

4.88 out of 5 average rating, 103 reviews

Cozy home. Comfy living

The whole group will enjoy access to everything from this centrally located home. three comfy bedroom, two bathrooms, large living room, dining and kitchen. close to the beach, nature reserved, kayaking, sky diving and Tanger outlet mall, restaurant and all the fast food located nearby. long island vast array of winery and farms stand etc. Guest is expected to follow house rules. 15 mins after check out time is given after that fees will incur at nightly rate

Guest favourite

Houseboat in North Fork

5 out of 5 average rating, 11 reviews

Peconic River Boatel

Perfectly updated nautical houseboat situated on the scenic Peconic River. Featuring two picturesque bedrooms, a full service eat-in kitchen and a living room with panoramic river view. Enjoy your morning coffee on the outside deck while taking in the sunrise. This historic waterfront town was named to Forbes Advisor’s “Best Places to Travel in 2023” — one of just 11 U.S. destinations on this year’s list. A must see for adventurers and families alike!

Guest favourite

Cottage in Pawling

4.98 out of 5 average rating, 120 reviews

Twin Lakes Designer A-frame Stone Cottage

*Twin Lakes Cottage* Stunningly restored 1930s a-frame stone cottage located on a private lake in West Mountain State Forest with a new deck, patio, soaring high skylights, and 21’ tall wood-burning fireplace. Resting on a hillside with 180 degree views of two lakes, this breathtaking retreat is a one-of-a-kind experience. Surrounded by mature oaks, ferns, and the soothing songs of birds, this remarkable home offers unmatched tranquility.