Cottage holiday rentals in Stamford

5 out of 5 average rating, 219 reviews

A quaint cottage is nestled among trees, featuring a covered porch with a railing. Colorful seasonal flowers adorn the entrance, leading to a gravel pathway. The driveway is lined with trees and offers ample parking space, creating a serene atmosphere in a wooded setting.

Cottage in Cortlandt

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

4.98 out of 5 average rating, 106 reviews

A spacious loft area features high ceilings with exposed beams and warm wooden accents. Two comfortable leather sofas face a central ottoman, surrounded by artwork and decor. Natural light floods in through large windows, highlighting the rich wooden floors and a decorative rug.

Cottage in Black Rock

Spacious Cottage Loft

Welcome to the Spacious Cottage Loft! Please enjoy a nice quiet relaxed atmosphere in this unique space. Its a little bit rustic with its shiplap pine and exposed beams. Its a little bit rock and roll with its little music space along with some favorite framed albums hanging on the walls. Very comfy queen size bed. 2 smart TVs (65" up & 55" down) for your entertainment pleasure. Roomy kitchen with brand new appliances. Bath-walk in shower. THIS SPACE IS DESIGNED TO ACCOMMODATE 1-2 GUESTS.

4.88 out of 5 average rating, 305 reviews

A striking wooden wall showcases a large bank of windows offering panoramic views of Lake Oscawana and surrounding foliage. The vaulted ceiling emphasizes the spaciousness of the room, inviting natural light to fill the space.

Cottage in Putnam Valley

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.

4.97 out of 5 average rating, 201 reviews

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

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

A welcoming living area features a comfortable couch and a textured ottoman, complemented by natural wood accents on the ceiling. Light fills the space from multiple windows, highlighting the hardwood floors and decorative stone wall that adds character to the room.

4.94 out of 5 average rating, 370 reviews

Winter 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.

A cozy living room is featured with a combination of a grey sofa and an orange couch. A decorative white coffee table rests on a patterned area rug, while a faux fireplace is accented by a round sunburst mirror and decorative items. Natural light enters through a nearby window.

4.99 out of 5 average rating, 154 reviews

3BD Cottage | Walk 2 Beach and Tyde Wedding Venue

Walking distance from Walnut Beach and Tyde Wedding Venue! Stay at this cozy 3-bedroom, 1-bath beach cottage in the heart of Walnut Beach. Perfect for family vacations, wedding guests, or Yale visitors, our modern farmhouse-style home features a full kitchen, a private backyard with a fire pit, and peaceful coastal vibes. Walk to the sand, celebrate at Tyde, enjoy coffee on the porch, and end the day by the fire. Comfort, style, and location — all in one unforgettable stay!

4.96 out of 5 average rating, 107 reviews

A spacious deck features a round table surrounded by four cushioned chairs, covered by a large red umbrella. Lush greenery and landscaped gardens are visible in the background, creating a serene outdoor setting.

Cottage in Seymour

3 Acre Forest, 2 King Beds, Fireplace, BBQ & more

🛏️2 king, 2 twin, BBQ, fireplace, firepit, 1550 sqft entire house 🅿️🛜 Tucked away at the end of a quiet street, set on 3+ acres of lush wooded land, our home is the perfect blend of seclusion and convenience. With a forest as your backyard and RT34 one min away, you can easily balance your desire for nature and adventure with the need for easy travel and commuting, take a short hike into a forest (trails minutes away) and/or relax under the stars around a fire pit.

4.96 out of 5 average rating, 260 reviews

A quaint cottage is nestled among vibrant trees, showcasing rich foliage in shades of green and burgundy. A well-kept lawn surrounds the cottage, with a white door framed by flower beds. The serene setting invites relaxation in a natural environment.

Cottage in South Salem

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 :)

4.96 out of 5 average rating, 211 reviews

A dining area features a long wooden table set for meals, with plates arranged on woven placemats. To one side, a bar area displays glassware and coffee equipment. Expansive windows frame scenic lake views, allowing natural light to brighten the space.

Cottage in Putnam Valley

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

4.95 out of 5 average rating, 262 reviews

A spacious living area displays rustic log walls and a mix of wooden and upholstered furniture. A comfortable leather sofa is positioned near a stone wood stove, while a colorful armchair adds charm. Natural light fills the room through windows adorned with patterned curtains.

Cottage in Patchogue

Quaint Cottage on Long Island's South Shore.

The Cottage is a lovely space enclosed in hedges for privacy on a one acre property. I do have 3 dogs, they are kept in a separate gated area on the property. The cottage is located 3 miles from downtown Patchogue which is enjoying a renaissance. There are many restaurants and cultural activities as well as ferry access to Fire Island (Davis Park) in the warmer weather. We are also the "Gateway" to The Hamptons.

Cottage in Fairfield Beach

4.98 out of 5 average rating, 126 reviews

Charming Fairfield Beach Cottage

Escape to our newly renovated waterfront cottage in Fairfield, just steps from a private beach on the Long Island Sound. This charming retreat is perfect for families and couples, offering a modern kitchen, private deck, and high-speed WiFi. Unique perk: Enjoy complimentary 24/7 access to a beautiful co-working space just 3 miles away. A perfect blend of relaxation and productivity awaits!

4.98 out of 5 average rating, 167 reviews

The cottage is nestled among lush greenery, with a sloping yard leading to a rock bed. Large trees partially shade the structure, which features a combination of dark shingles and white trim. Windows allow soft light to illuminate the interior, enhancing the tranquil surroundings.

Cottage in Danbury

Fern Grove Cottage

If you’re looking for tranquility, this is the place for you! This charming cottage is located on a secluded country road. The cottage sits at the back of a gorgeous park-like property, and is near parks with hiking trails. This antique cottage has many modern renovations, providing convenience and comfort while maintaining the historic charm. This is the perfect getaway!

Popular amenities for Stamford cottage rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

Cottage in Newtown

4.91 out of 5 average rating, 11 reviews

Magical Lakeside – Lake Zoar Views & Private

4.92 out of 5 average rating, 63 reviews

A private hot tub is situated on a rocky terrace surrounded by trees, with views of the lake in the background. The area is enhanced by natural textures, including stone and moss, creating a serene outdoor space for relaxation.

Cottage in Patterson

The Silent Sun Cottage Hottub/Skiing/Firepit/Lake

5 out of 5 average rating, 9 reviews

The living area features a comfortable sofa adorned with a striped throw, a coffee table, and a television. Nearby, a dining space is set for meals, with natural light illuminating the room through large windows framed by light curtains.

Cottage in Bellport

Bellport Inn, Charming Cottage in the Village!

A welcoming entrance features a pathway of gray stone leading to a blue cottage with large windows. Flanking the path are colorful garden beds and a grassy lawn. A set of stairs leads up to the front door, painted a cheerful blue.

Cottage in Fairfield Beach

4.8 out of 5 average rating, 10 reviews

The Lil Nauti Cottage, Steps To Fairfield Beach

4.93 out of 5 average rating, 27 reviews

A large gunite pool is surrounded by a well-maintained grassy yard, featuring comfortable lounge chairs on a sunbathing area. Lush trees provide shade, while a charming cottage stands in the background, contributing to a serene outdoor setting.

Cottage in Bellport

Renovated Historic Cottage w/ Pool Bellport Vllage

Pet-friendly cottage rentals

4.96 out of 5 average rating, 54 reviews

A bright living room features large windows displaying a colorful sunset. A plush sectional sofa, dressed with several cushions, surrounds a round coffee table. A textured area rug adds warmth to the space, enhancing the inviting and comfortable atmosphere.

Cottage in New Fairfield

Sunset Cabin Modern Home Kayak FirePit Lake Access

4.94 out of 5 average rating, 79 reviews

The exterior of the cottage is illuminated by warm lights, showcasing a welcoming entrance framed by lush greenery and flowering plants. The architecture features a peaked roof with large windows that allow for natural light. A paved path leads towards the front door.

Cottage in East Norwalk

Seaside Serenity: 2B 1B, Patio,Near Beach

4.85 out of 5 average rating, 200 reviews

The outdoor area is illuminated by soft lights, creating a relaxing atmosphere against a backdrop of tall trees. Lounge chairs are positioned on the deck, accompanied by a small table. The cozy cabin features multiple windows, giving a warm ambiance during the evening.

Cottage in Carmel Hamlet

Lake Cabin Escape Firepit•Fenced yard•Dogs welcome

5 out of 5 average rating, 19 reviews

A charming cottage is set against a backdrop of lush green trees and an expansive sky. The structure features a covered porch with white railings, providing a welcoming entrance. Stone steps lead to the yard, which is surrounded by well-maintained grass.

Cottage in New Canaan

Peaceful New Canaan 2-BdRm Cottage - Pet Friendly!

4.96 out of 5 average rating, 25 reviews

A charming cottage is set against a backdrop of lush greenery, featuring a stone staircase leading to the entrance. Two outdoor chairs are positioned near the stairs, inviting relaxation. The property is surrounded by trees, enhancing the serene environment.

Cottage in Southbury

Sun Filled Cottage

The exterior of a beach cottage is shown, featuring light-colored siding and blue shutters. A white railing surrounds a small porch, leading to a front door. Lush greenery and a few decorative elements enhance the inviting appearance of the home.

4.93 out of 5 average rating, 137 reviews

SILVER SANDS BEACH COTTAGE MILFORD NEAR YALE/TRAIN

Cottage in Port Jefferson Station

A charming cottage with a red exterior is surrounded by a lush garden filled with various plants and flowers. A spacious covered porch extends across the front, offering a welcoming entryway. The well-manicured lawn is complemented by vibrant greenery and colorful blooms, creating a pleasant outdoor space.

4.8 out of 5 average rating, 514 reviews

The Red Cottage Circa 1936

Superhost

A large willow tree extends gracefully over the calm waters of Lake Waccabuc, framing a peaceful view of the surrounding autumn foliage. Stone patio chairs offer a place to relax, while a small fire pit rests on the grassy shore, creating an inviting outdoor space.

Cottage in South Salem

4.85 out of 5 average rating, 48 reviews

Charming Lake Front Cottage - Paradise Rest Home

Private cottage rentals

4.97 out of 5 average rating, 107 reviews

A charming two-story cottage is surrounded by trees, with a lush green hillside in the backdrop. The driveway leads to a garage with two entrance doors. An outdoor staircase ascends to the living area, illuminated by dappled sunlight filtering through the leaves.

Cottage in Pawling

Forest Acres Cottage: Appalachian/Empire St Trail!

4.96 out of 5 average rating, 102 reviews

The exterior of the cottage is depicted, featuring a welcoming porch area with seating. A fire pit is framed by several outdoor chairs on a grassy lawn. Green trees provide a natural backdrop, and the cottage's light-colored siding reflects a sunny daytime atmosphere.

Cottage in Brentwood

The Comfy Cottage

4.98 out of 5 average rating, 114 reviews

A private deck overlooks a tranquil marsh, framed by vibrant flowers in terracotta pots. A shaded seating area includes a couch with cushions and a small table, inviting relaxation while enjoying the serene view of the water and surrounding natural greenery.

Cottage in Short Beach

Enchanted Cottage on the Marsh, walk to beach

Superhost

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.

4.87 out of 5 average rating, 94 reviews

Cheerful 3 Bedroom Cottage with Fire Place

4.82 out of 5 average rating, 192 reviews

The exterior of a private cottage is presented, showcasing a gray wood-paneled facade with a light-colored front door. Well-maintained landscaping includes shrubs and grass, leading to a concrete pathway. A wooden fence and trees provide a natural backdrop.

Cottage in Kings Park

Cozy Riverside Cottage

5 out of 5 average rating, 27 reviews

The sunset is reflected on calm waters, creating a warm glow. A wooden railing is visible in the foreground, with a table and chair set positioned to enjoy the view. Rocky shoreline is seen in the distance, near the horizon where the sun dips below.

Cottage in Lordship

Connecticut Beach Cottage

5 out of 5 average rating, 121 reviews

A charming white cottage is surrounded by well-maintained landscaping, featuring lush green grass and various shrubs. A stone wall borders the garden, and a large window with decorative accents is visible, inviting natural light into the space.

Cottage in Redding

Star Cottage