Cottage holiday rentals in Stamford

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Popular amenities for cottage rentals in Stamford

Cottage rentals with a hot tub

Superhost
Cottage in Guilford
4.95 out of 5 average rating, 178 reviews

Luxury cottage by the sea with hot tub and pool

MichelleRating, 5 stars1 month ago
Wonderful for a peaceful weekend away. The views were beautiful, the space was clean (with amazing climate control), and the hot tub area was very user friendly. I would definitely stay again! Highly recommend the short walk to Chaffinch Island Park to check out the tide pools.
Superhost
Cottage in Greenwood Lake
4.84 out of 5 average rating, 206 reviews

Cozy Cottage | HotTub & Family Rm | 1H fr NYC

CheyenneRating, 5 stars1 day ago
Beautiful home! I loved the stay very peaceful, definitely will be returning soon and the host was very lovely.
Superhost
Cottage in Plymouth
5 out of 5 average rating, 13 reviews

Summer Escape w/ Cool Tub + Lake Access

AnanyaRating, 5 stars1 week ago
Our family of five loved staying at Yoka and Val's place. The location is very quiet with a peaceful pond across the street. The house itself is very clean and comfortable with everything you need - towels, soap, shampoo, conditioner, coffee and spices - easily available. The beds were also very comfortable. The best part, of course, was the private hot tub in the back yard. It was set in a canopy for extra privacy and wind protection. We loved it. We would definitely stay here again if in the area.
Superhost
Cottage in Greenwood Lake
4.97 out of 5 average rating, 114 reviews

Romantic Experience Secluded Lake House + Hot Tub

TaylorRating, 5 stars5 days ago
Chateau René is the perfect peaceful escape. The home cozy and well maintained - exactly as pictured. The view made every morning feel like a dream. René was so warm, responsive, and accommodating. He shared great local recommendations and clear instructions for the house, which made settling in a breeze. The most special part of my stay was getting engaged here! René secretly coordinated with my now-fiancé and friend to make it all happen. His excitement and willingness to help meant a lot to us. Overall, 10/10 stay. We’ll definitely be back!
Superhost
Cottage in Highland Lakes
4.97 out of 5 average rating, 322 reviews

The Mountaintop Lakehouse that Time Forgot.

NathanRating, 5 stars6 days ago
A hidden gem! This spot has a ton of character and the hosts are awesome! The lake and surrounding area is beautiful as well, with plenty to do for the outdoorsy type and cute shops and great restaurants within minutes. would highly recommend and hope to find time for a return trip!
Superhost
Cottage in Bellport
4.93 out of 5 average rating, 27 reviews

Renovated Historic Cottage w/ Pool Bellport Vllage

KellyRating, 5 stars7 months ago
Tabitha's place was perfect for our group stay. Right in the middle of town and perfect for what we needed for the week!
Superhost
Cottage in Bethlehem
4.98 out of 5 average rating, 102 reviews

Cozy Getaway | Pet Friendly | Litchfield Cty

LyndaRating, 5 starstoday
Kelsey’s cottage was exactly as described. It was so beautifully decorated & had everything that we would need. We had a wonderfully relaxing weekend & hope to do it again soon.
Superhost
Cottage in Cold Spring
4.79 out of 5 average rating, 219 reviews

Cozy Countryside Cabin Spa/Fireplace/Enclosed Yard

AlexanderRating, 5 stars2 weeks ago
The house is well maintained and clean. The kitchen was well stocked with everything needed to cook/grill. The hot tub was pleasant and the backyard was great for our kids. The location is only about 7 minutes from downtown Cold Spring and 15-20 minutes from Beacon. The location was ideal for wanting a mix of peace and quiet with accessibility to local attractions.

Pet-friendly cottage rentals

Top guest favourite
Cottage in Cornwall
5 out of 5 average rating, 52 reviews

Carriage House: Romantic Hideaway near West Point

LeAnnRating, 5 stars1 week ago
The adorable carriage house was just perfect for my husband and me and our dog! We were in town for a wedding, a visit with our son, and a retirement ceremony, so we stayed for over a week. The house was cute, clean, spacious, and located in the lovely town of Cornwall. We went for walks in the morning through the town, worked from the house during the day, and went out in the evening into neighboring towns. It was very close to Beacon and West Point where some of our activities were. Catherine and Jay were wonderful hosts and we would love to stay here again and also venture out to one of their other properties that they host!!
Top guest favourite
Cottage in Putnam Valley
4.94 out of 5 average rating, 82 reviews

Charming Cottage Retreat | Grill & Steps to Lake

Jo AnnRating, 5 stars3 weeks ago
Tech savvy home. All the right plugs for our electronics. Heated bathroom floor a plus during cold weather. Upstairs bedroom had hanging space and dresser, but neither available in lower bedroom. Did have luggage rack in lower bedroom. Definitely a do again for me!
Guest favourite
Cottage in Poughkeepsie
4.91 out of 5 average rating, 347 reviews

Be in Nature at this Gorgeous Riverfront Cabin

MichelleRating, 5 stars1 week ago
Second time staying at Mark’s place and doesn’t disappoint! Quiet serene natural setting with all the convenient amenities of a home away from home
Guest favourite
Cottage in Pine Bush
4.89 out of 5 average rating, 264 reviews

Seclusion and Romance - Hot Tub is hot hot hot

KemoneRating, 5 stars2 months ago
Nice little getaway during the cold season. The hot tub was excellent and about 100 degrees so perfect even with the cold temperature. It was still possible to put together a meal with the propane grill and warm things up in the microwave or store them away in the fridge. The heat was excellent in the space. Seems like it would be a great place to stay in the summer as well!
Top guest favourite
Cottage in Patchogue
4.94 out of 5 average rating, 233 reviews

Quaint Cottage on Long Island's South Shore.

TylerRating, 5 stars2 weeks ago
Leah was an incredible host, but a bit nervous at first. Our stay was absolutely amazing, and our dogs felt right at home in their cozy cottage. It was such a cute and comfortable place, and we’re so glad we chose Leah as our host. She went above and beyond for us during our stay.
Guest favourite
Cottage in Newtown
4.93 out of 5 average rating, 243 reviews

Private and Serene home close to I-84 and shopping

TonyRating, 5 stars1 week ago
We were looking for a last minute peaceful four day getaway and we found it here. We can’t stop talking about it. Although relatively close to everything we felt as if we were in the middle of a forest. The only sounds were the chirping of song birds and a woodpecker in the morning. Local restaurants are great and for us a trip to Yale University’s free museums and nearby antique shops rounded things out. The house is charming and Rio, our host , made sure we had everything. The few things we forgot from home were there! Wonderful experience all around.
Guest favourite
Cottage in Guilford
4.93 out of 5 average rating, 268 reviews

Charm + location. Walk to beach, town, & harbor.

JaneRating, 5 stars1 week ago
This is a great place to stay. It’s lovely and very conveniently located for the town of guilford and the beach. It’s like staying at a friend’s place, an extremely thoughtful friend who has considered what would make you feel comfortable and welcomed. This is our second stay here and it is one of our favorite air B&B experiences. Jeanne is so considerate and responsive, and has the house perfectly prepared. Stay here if you can.
Top guest favourite
Cottage in Redding
4.93 out of 5 average rating, 259 reviews

Cozy Cottage by the pond

MaryEllenRating, 5 stars2 weeks ago
My husband and I had a great stay. James and Rose are super helpful hosts. It’s a great place to relax and enjoy nature. Walking distance to a lovely park they recommended with tons of hiking trails and very quiet.

Private cottage rentals

Superhost
Cottage in Cold Spring
4.96 out of 5 average rating, 23 reviews

Romantic Private Lake Art-Deco Cabin Hudson Valley

JamesRating, 5 stars10 months ago
The area was absolutely beautiful. Valhalla Lake was private with stunning views. The cabin was exactly as it was described and the book of directions that was left for guidance was easy to follow.
Top guest favourite
Cottage in Middletown
4.97 out of 5 average rating, 71 reviews

⌂ Backyard Porch ⌂ Cozy Getaway ⌂ Catskills Hikes

Adryanna IlysseRating, 5 stars1 month ago
This charming cottage in Upstate NY is the perfect escape from city life. Surrounded by towering trees and nature’s tranquility, it offers a cozy, welcoming retreat. Inside, the rustic decor, soft lighting, and warm bed create the ultimate cozy atmosphere. The well-equipped kitchen and plush bed ensure comfort, making it easy to relax. The outdoor space is a highlight—sip coffee on the porch, stargaze , or explore nearby hiking trails. Whether you’re a couple, solo traveler, or small family, this peaceful retreat is a must-visit. Highly recommended!
Guest favourite
Cottage in Pawling
4.97 out of 5 average rating, 97 reviews

Forest Acres Cottage: Art East is soon! May 3 - 4

Bill McGoughRating, 5 stars1 week ago
Great place to stay when in the area. It’s become our ‘go to’ stay!!
Guest favourite
Cottage in Brentwood
4.96 out of 5 average rating, 67 reviews

The Comfy Cottage

AmberRating, 5 stars4 weeks ago
Well thought out space. Quiet neighborhood. Has all the essentials needed for vacation. There is a chair in the bedroom that converts into a small single bed for a child. Nice backyard space.
Superhost
Cottage in North Fork
4.92 out of 5 average rating, 52 reviews

Beautiful cottage on East End

AshleyRating, 5 stars5 months ago
Vincent’s place was great for my husband, myself, our baby and my parents to stay when visiting Jamesport for a wedding. Beautiful cottage, close to everything, and Vincent was very easy to communicate with. Would stay here again
Superhost
Cottage in Milford
4.78 out of 5 average rating, 32 reviews

Cheerful 2 bedroom cottage on beach

MatthewRating, 5 stars9 months ago
This house is absolutely perfect. It's clean, charming, has everything you need. The beautiful back yard has plenty of space and good stuff for kids to play with. Also, it's about a 30 second walk to the beach... neighbors are out on their patch of beach but yours is yours to yourself. It's perfect. We cannot wait to come back.
Superhost
Cottage in North Fork
4.91 out of 5 average rating, 53 reviews

Cottage in Calverton

KaitlynRating, 5 stars8 months ago
Perfect for our weekend getaway. Very clean and relaxing and close walk to a cute little beach. We would stay here again!
Superhost
Cottage in Pound Ridge
4.82 out of 5 average rating, 62 reviews

Pound Ridge Paradise: Your Private Cottage Retreat

SimiRating, 5 stars1 month ago
we love Walkers place and do come here twice a year. it's a beautiful home, it's so zen, so pretty, so clean, we just absolutely love it. it's a great fabulous house and spot to stay. ♥️

Destinations to explore