
Cottage holiday rentals in Stamford
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Nightly prices starting at
Stamford holiday rentals start at £97 per night before taxes and fees

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Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Stamford rentals

4.7 Average rating
Stamford stays receive an average rating of 4.7 out of 5 from guests
Top-rated cottage rentals in Stamford
Guests agree: these cottages are highly rated for location, cleanliness and more.

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
5.0 out of 5 average rating, 230 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
Lakefront Cottage near Hudson Valley
Named in the Top 30 U.S. Lakehouse Rentals by Refinery29 in May'21, this beautiful, secluded cottage on pristine Lake Oscawana has breathtaking views. Escape the city and enjoy the fresh country air! Extra-large great room, cathedral ceilings, loft bedroom, kitchenette, bathroom, fireplace, wall of double-height windows with spectacular lake views. Central AC/heat, hardwood floors, private large deck with BBQ. Dock nestled in a cove where you can swim or paddleboard. Only 1 hour from NYC.
4.89 out of 5 average rating, 332 reviews
3BR Cottage Walk to Beach and Tyde Wedding Venue
Walking distance from Walnut Beach and Tyde Wedding Venue! Stay at this cozy 3-bedroom (King, Queen + Twin), 1-bath beach cottage in the heart of Walnut Beach. Perfect for family vacations, wedding guests, or Yale visitors, the cottage features a full kitchen, private backyard, fire pit, and peaceful coastal vibes. Walk to the sand, celebrate at Tyde, enjoy coffee on the porch, and relax by the fire pit. Firewood is not provided. Comfort, style, and location — all in one unforgettable stay!
4.99 out of 5 average rating, 181 reviews
Oscaleta Guest House: Lakefront Cabin
Escapology-A spectacular lakeside destination, designed as a luxury suite with its own dock. Close to NYC and ideal for a quick trip, remote work or an extended retreat. Glamping-A cabin in the woods on a lake surrounded by nature, but tech-enabled with all the modern perks. Artfully Designed Space-Modern retrofit thoughtfully curated with custom artwork throughout this historic 1920's cottage. Purpose built for your outdoor routine- from grill to canoe…. We recommend 3+nights if you can.
5.0 out of 5 average rating, 140 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
4.97 out of 5 average rating, 246 reviews
Summer Sale! CozyCottage/Pet-friendly/ WalktoBeach
Inspired by my Dad's wanderlust and love of sea & sand. Relax and unwind in this completely remodeled, stylish Cottage a block and a half from Long Island Sound and .9 mile to Walnut Beach - walk to coffee, pizza, lobster shack! We offer a modern kitchen, breakfast nook, dining area, natural stone wall, parking and W/D. Located in a charming coastal town - enjoy quiet neighborhood walks, coastal trails, boardwalk, breweries and restaurants. 15 min to Yale/New Haven, 65 mi to NYC.
4.94 out of 5 average rating, 421 reviews
Serene lake front cottage 1 hour from NYC
Serene minimalist cottage directly on Lake Oscaleta with spectacular waterfront and Mountain Lakes Park behind. Quiet, isolated and lost in the trees, you feel you are in Vermont or the Adirondacks. Yet it's only 1 hour from Manhattan, 10 minutes from restaurants. Kayak, canoe, fish, paddleboard. Cottage is elegant, cozy and winterized warm and the lake is effectively empty in the fall/winter/spring. Please note: because of an asthmatic child, we cannot accept any animals.
4.97 out of 5 average rating, 149 reviews
Private cottage in horse country &1 hour from NYC!
Private cozy cottage located in horse country on the the NY/CT borders ( New Canaan, Ridgfield, Wilton ) It is a perfect quiet getaway for couples or a friends night out , a great pit stop for travelers /skiers , fine dining , shopping /antiquing , Ridgefield Playhouse , hiking ,and a short ride to Grace Farms . 1 hour train ride to NYC . We provide organic fruit,breakfast snacks, coffee and tea . It is your home away from home and more :)
4.95 out of 5 average rating, 283 reviews
Private Lake House 1 Hour to NYC & Near Westpoint
Escape to this private lake cottage. Just 1h drive from NYC, near lots of skiing & hiking Thunder Ridge (30mi) Mt Peter (30mi) Victor Constant (20mi) Campgaw Mountain (40mi) Enjoy panoramic lake views, 86in TV, ample board games, 5-jet shower, and indoor jetted Jacuzzi tub. Short drive to Bear Mountain & West Point. Legoland is 45 min away Pets are welcome! WiFi is extremely fast and we have free electric car charging
4.96 out of 5 average rating, 252 reviews
Modern Country Cottage by Bear Mountain
Wake up feeling rejuvenated in a lofted bedroom beneath a wood-paneled ceiling with skylight windows. Descend a spiral staircase into a warm kitchenette for a cup of coffee, then have a seat in an airy living room beside a brass-plated decorative fireplace. Enjoy a picnic or grill on the front lawn with your pet, and explore four acres of Hudson Valley landscape shared with the main house next door.
4.97 out of 5 average rating, 229 reviews
Cozy Riverside Cottage
This is a private cottage on its own lot with its own driveway and yard located in a quiet residential neighborhood. Several grocery stores and restaurants for delivery/pick up in the area. 400 MBPS Internet connection for those who need a reliable internet connection for work/movie streaming! Please note guest maximum is 4. There are no additional guests or visitors allowed.
4.83 out of 5 average rating, 201 reviewsPopular amenities for cottage rentals in Stamford
Cottage rentals with a hot tub

Lakefront Hudson Valley Cottage w/Hot Tub/Fire Pit
4.92 out of 5 average rating, 72 reviews
Between A Lake & Pond - Tranquil Cottage Haven

Sumak-Kawsay · Lake front Hot Tub CT
5.0 out of 5 average rating, 20 reviews
The Lil Nauti Cottage, Steps To Fairfield Beach
4.86 out of 5 average rating, 14 reviews
Renovated Historic Cottage w/ Pool Bellport Vllage
4.93 out of 5 average rating, 28 reviews
Bellport Inn, Charming Cottage in the Village!
5.0 out of 5 average rating, 9 reviewsPet-friendly cottage rentals

Spacious Cottage Loft
4.98 out of 5 average rating, 114 reviews
3 Acre Forest, 2 King Beds, Fireplace, BBQ & more
4.97 out of 5 average rating, 149 reviews
The Red Cottage Circa 1936
4.8 out of 5 average rating, 557 reviews
Cozy Cottage by the pond
4.93 out of 5 average rating, 300 reviews
Lake Cabin Escape Firepit•Fenced yard•Dogs welcome
4.87 out of 5 average rating, 231 reviews
Cozy 2 Story Cottage in Short Beach Community
4.85 out of 5 average rating, 271 reviews
Private and Serene home close to I-84 and shopping
4.92 out of 5 average rating, 329 reviews
Solitude | Deck | Record Player by Mosaic Getaways
4.96 out of 5 average rating, 122 reviewsPrivate cottage rentals

Cheerful Private 3 Bedroom Cottage in Cold Spring
4.93 out of 5 average rating, 195 reviews
Water Views & July 4 Fireworks – June 27, 2026
4.98 out of 5 average rating, 181 reviews
Getaway On Grove – Cozy Cabin by the Lake
4.93 out of 5 average rating, 99 reviews
Enchanted Cottage on the Marsh, walk to beach
4.97 out of 5 average rating, 139 reviews
Forest Acres Cottage: Appalachian/Empire St Trail!
4.97 out of 5 average rating, 116 reviews
The Comfy Cottage
4.94 out of 5 average rating, 128 reviews
Cozy cottage in the village of Pound Ridge
4.96 out of 5 average rating, 79 reviews
Cos Cob Cottage- Full Kitchen, Pet Friendly
4.89 out of 5 average rating, 9 reviewsDestinations to explore
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