Holiday rentals in Stamford

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Top-rated holiday rentals in Stamford

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

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Guest favourite
The well-appointed bedroom features a comfortable bed with plush pillows and a decorative throw blanket. Natural light filters through large windows, creating a serene ambiance. A stylish mirror stands nearby, and warm bedside lamps flank the bed, enhancing the cozy atmosphere.
Flat in Stamford
4.97 out of 5 average rating, 70 reviews

Stamford Grand Apartment + Cozy Den

Welcome to your luxurious One-Bedroom + Den home at The Asher in downtown Stamford. Enjoy the vibrant city life with cafes, brunch spots, bars, and fine dining just steps away on Bedford Street. Highlights: • Request to be on the 4th floor or higher • Deep-clean before every guest • Coffee, fresh linens, & bathroom essentials provided • Co-working Lounge & Conference Rooms • 24/7 Fitness Centre & Yoga Room • Rooftop Pool and Lounge • Outdoor Grill Stations • LED recessed lighting

Top guest favourite
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
4.97 out of 5 average rating, 186 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

Top guest favourite
The cottage is nestled among lush trees, highlighted by a distinctive stone chimney. Expansive glass doors reflect the surrounding greenery, inviting natural light inside. The structure is surrounded by verdant shrubs, creating a harmonious connection with nature.
Guest house in Pound Ridge
4.94 out of 5 average rating, 103 reviews

A Lovely Cottage in the Woods

Welcome to our cottage located just 1 hour north of NYC! It is nestled into 2.7 acres of beautiful gardens, mossy groves, and lovely woods. Nature abounds: The property abuts the 4000 acres of the Ward Pound Ridge Reservation. A trailhead begins right across the driveway. The cottage is equipped with a stone fireplace, spacious kitchen, living room area, table for dining and working, and a sleeping loft. During the summer, a private salt water pool is available.

Superhost
A well-equipped kitchen features wooden shelves with dishes and a coffee maker. A modern sink and black faucet are complemented by a smooth countertop, while natural light filters through a window adorned with greenery. Kitchen essentials are organized for convenience.
Flat in Brookfield
4.92 out of 5 average rating, 293 reviews

Peaceful apartment on 3.5 acres w/ Artist studio.

Welcome to our cozy apartment! This fully enclosed apartment is attached to our main house on a beautiful 3.5-acre property in Brookfield. Enjoy a kitchen, comfortable living and bedroom area, and a clean bathroom. Guests have access to a shared 32 ft, 10 ft deep pool, artist studio, pool table,, garden, fire space, and outdoor seating. We provide a guidebook for your convenience. Book now and experience a perfect blend of comfort, creativity, and relaxation.

Guest favourite
A well-lit living room features a light-colored sofa adorned with cushions, paired with a wooden coffee table. A television is mounted on the wall, while a glass-fronted cabinet displays decorative items. Light streams through large windows, highlighting the warm wooden floor.
Home in Stamford
4.84 out of 5 average rating, 189 reviews

Gem by the water+ firepit and all fenced backyard

Take it easy at this unique and tranquil getaway. One block away from the water and three blocks away from Dolphin Cove. Enjoy walkings and site-seeings. Perfect for going kayaking, paddle boarding or just stay relaxing in the backyard. It is located at 5 minutes walking distance from the train station and 7 minutes away from downtown. Bus stop in front of the house. The house has a lower level that mostly is occupied by the host and sometimes with guests.

Guest favourite
A spacious room features warm hardwood floors and large windows allowing natural light. A king size bed is adorned with light bedding and soft pillows. A comfortable sofa can be seen in the background, alongside a wooden coffee table and plants, fostering a relaxed atmosphere.
Flat in Stamford
4.94 out of 5 average rating, 53 reviews

Spacious. Water Views & Access. Steps to Beach.

Spacious apartment with King Size Bed. Direct access to Cove Pond & Long Island Sound. Easy access to downtown Stamford, Stamford Train Station & Manhattan. A few steps away from Cove Island Beach & Park. Apartment features high ceilings, central heating & cooling, brand new washer & dryer, hardwood floors, formal dining room and 60" HDTV with Amazon Fire TV. Guests have complimentary access to YouTube TV (comparable to cable), Peacock, & Prime Video.

Guest favourite
The balcony features a charming outdoor dining set with a table and two folding chairs. A spread of sliced bread, apples, and glasses of sparkling drink is arranged, overlooking a view of downtown Stamford, with a mix of buildings and greenery visible in the distance.
Flat in Stamford
4.89 out of 5 average rating, 129 reviews

Honey Spot Studio | Downtown City Views

Enjoy a stylish experience at this centrally-located spot in the heart of downtown Stamford. Walk downtown to enjoy all it has to offer, from restaurants, shopping, UCONN of Stamford and more! A short train ride to New York City, our apartment offers everything you need for a comfortable stay in the area. We offer free parking on the premises and the train station is a 10 minute walk. Washer and Dryer included in the building with credit card payment.

Top guest favourite
A spacious living area features a deep blue sofa adorned with decorative pillows. The wall behind is an artistic display of wooden frames in various sizes and shapes, creating a textured backdrop. Natural light enters through large glass doors, illuminating the inviting interior.
Flat in Stamford
5 out of 5 average rating, 40 reviews

The Gallery in Downtown Stamford

Step into The Gallery, a stunning 1BR, 1BA luxury retreat in Downtown Stamford. This sophisticated haven blends artistic elegance with modern comfort, featuring striking design and unique furniture reminiscent of an upscale gallery. Unwind on the private balcony with breathtaking city views. Perfect for business or leisure travelers, The Gallery offers a serene escape above the city's energy. Experience refined elegance in this one-of-a-kind retreat.

Guest favourite
A spacious bed is adorned with soft neutral linens and decorative pillows in warm tones. Light-colored side tables with lamps are placed on each side, and framed beach photographs are displayed on the wall above. A mirror reflects the inviting atmosphere in the room.
Flat in Stamford
4.95 out of 5 average rating, 109 reviews

Cozy King BR | Walk to beach | Close to downtown

Welcome to the Lounge on Webb! Your cozy, little private oasis! It’s the perfect stay located just 10 minutes from Stamford’s downtown area and walking distance to Cove Beach and Chelsea Piers. Conveniently located just 40 minutes from NYC by train or car, you can spend your day exploring the Big Apple! Whether you’re here for business or leisure, this apartment provides the perfect blend of comfort and convenience!

Guest favourite
A spacious living area features a gray sectional sofa and a large flat-screen TV mounted on the wall. Sunlight enters through small windows, and plants are arranged on ledges. A small table for activities is neatly positioned on a light-colored rug.
Flat in Stamford
4.78 out of 5 average rating, 55 reviews

Apartment for rent Stamford CT

Cozy and Private Basement Apartment for Rent – Perfect for Families, Couples, or Small Groups! Escape to a beautiful and peaceful retreat in this spacious basement apartment, offering total privacy with its own entrance on a quiet dead-end street. Perfectly located near Route 15 (Merritt Parkway), you'll enjoy both tranquility and convenience during your stay.

Superhost
A cozy living area is present, featuring a neutral-colored sofa draped with an orange throw. A round glass coffee table is positioned in front of the sofa, set on a patterned area rug. Natural light filters through sheer curtains, illuminating the blue walls decorated with artwork.
Flat in Glenbrook
4.78 out of 5 average rating, 204 reviews

Downtown "Blue Nest" apartment

Cozy, adorable, updated and fully decorated 1 bedroom apartment in a downtown building with garage & 24 hours security. Equipped with everything you might need. Come stay with us and discover Stamford through the eyes of a local talented artist. There are certain things about the building that I can't change - please read the whole description before booking

Top guest favourite
Home in West Side
4.99 out of 5 average rating, 180 reviews

STAMFORD STUDIO CLOSE TO DOWNTOWN AND SHOPPING

Welcome, to newly renovaded small studio for one guest with private entrance, bathroom, small kitchen with microwave, coffee maker and refrigerator. Off the street parking, you have your spot reserved during your stay. One mile from I-95, walk to shopping and restaurants, five minutes drive to Stamford downtown.

Popular amenities for Stamford holiday rentals

When is the best time to visit Stamford?

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Frequently Asked Questions

  • Where should I stay in Stamford?

    Make yourself at home in Stamford by choosing from our most frequently booked neighborhoods. We have over 520 vacation rentals in Old Greenwich, over 520 vacation rentals in New Canaan, and over 170 vacation rentals in Cos Cob.

  • Are there vacation rentals with a dedicated workspace in Stamford?

    Yes! Work meets play with ease at over 340 vacation rentals in Stamford featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Stamford?

    Four-legged friends are welcome in Stamford. Choose from more than 200 vacation rentals for guests traveling with pets.

  • Are there Stamford vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 110 vacation homes with pools in Stamford, available on Airbnb. Make a splash and soak up the sun in style!

  • How much does it cost to stay in house rentals in Stamford?

    Experience the best of Stamford with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do apartment rentals in Stamford have self check-in?

    Absolutely! We offer over 20 apartment rentals with self check-in in Stamford. Enjoy a tailored experience with all the comforts you desire.

  • Do townhouse rentals in Stamford have wifi?

    Absolutely! We offer over 10 townhouse rentals with wifi in Stamford. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Stamford have a gym?

    Absolutely! We offer over 40 house rentals with a gym in Stamford. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Stamford have a bbq area?

    Absolutely! We offer over 50 house rentals with a bbq area in Stamford. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in Stamford?

    Stamford has more than 180 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

Quick stats about holiday rentals in Stamford

  • Total holiday rentals

    Explore 500 holiday rentals in Stamford

  • Nightly prices starting at

    Stamford holiday rentals start at $39 SGD per night before taxes and fees

  • Verified guest reviews

    Over 16,400 verified reviews to help you choose

  • Family-friendly holiday rentals

    180 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 200 rentals that welcome pets

  • Holiday rentals with a pool

    110 properties feature pools

  • Rentals with dedicated workspaces

    340 properties have a dedicated workspace

  • Wifi availability

    500 of Stamford holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Self check-in, Gym and BBQ grill across Stamford rentals

  • 4.8 Average rating

    Stamford stays are highly rated by guests – averaging 4.8 out of 5!