Cottage vacation rentals in Greenwich

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Popular amenities for Greenwich cottage rentals

Cottage rentals with a hot tub

Cottage in Ocean Beach
5 out of 5 average rating, 18 reviews

Charming and Adorable Beach Cottage

LisaRating, 5 stars24 months ago
Louise's place was perfect. Louise was so easy to communicate with, super responsive, kind, thoughtful and truly appreciated that she had the option of flexible dates (instead of so many sat to sat or sun to sun requirements in summer). The cottage was cozy, cute, spotless & well stocked. My teenage kids loved the hot tub (as it was a bit chilly in the evenings) and I loved the outdoor shower. We loved having the bikes to take rides around the Island and loved the location. Our only regret is that we didn't get to stay there longer! We will definitely try to stay at Old Snuggler again!
Superhost
Cottage in Greenwood Lake
4.84 out of 5 average rating, 210 reviews

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

Daphne FiguereroRating, 5 stars6 days ago
We booked the house for five nights for a group of six adults and had a lovely visit. Gabriela was a fantastic host communicating super promptly to our questions. It rained 90% of the time so we used the interior of the house to the fullest, and not the exterior (no fire pit, bikes, or hot tub) so cannot comment on those features. All appliances worked well. Kitchen is helpfully labeled and well stocked with kitchenware. The beds were very comfortable, towels fluffy, and downstairs family/game room is a great space for all ages. Furniture was comfortable, dining table was welcoming and though the house shows a bit of wear and tear here and there, everything was clean, tidy, and decorated appealingly. Tip: Bellvale Market just 7” away had great quality food products; Warwick, a quaint larger town, is just 10-15” away providing all other conveniences.
Top guest favorite
Cottage in Greenwood Lake
4.97 out of 5 average rating, 116 reviews

Romantic Experience Secluded Lake House + Hot Tub

KristyRating, 5 stars4 weeks ago
The Chateau Renee was a great place to stay! From the scenic view from the back deck and hot tub, to the beautifully curated interior, our small group had an amazing time. We enjoyed some local restaurants in Greenwood Lake and over in Warwick, and were able to catch a broadway show in the city since we were only about an hour away. If you’re looking for a spot to stay anywhere in this area, you have found your Airbnb!
Top guest favorite
Cottage in Bellport
4.93 out of 5 average rating, 27 reviews

Renovated Historic Cottage w/ Pool Bellport Vllage

KellyRating, 5 stars8 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 Cold Spring
4.79 out of 5 average rating, 227 reviews

Cozy Countryside Cabin Spa/Fireplace/Enclosed Yard

LoisRating, 5 stars3 days ago
Secluded cozy cottage minutes from downtown Cold Spring. Nice fenced in yard, dog and kid-friendly. Bed large and comfy. Loved the peacefulness.
Superhost
Cottage in Patterson
4.9 out of 5 average rating, 52 reviews

The Silent Sun Cottage Hottub/Kayak/Firepit/BBQ

AleksandreRating, 5 stars3 weeks ago
The Silent Sun Cottage is a very charming & peaceful home for a getaway. Everything is modern, clean, nicely decorated, and well stocked. James & Abigail are lovely hosts that made us feel welcome and special. The best part was spending time in the back yard (back yard does not do it justice) on the hammocks or sitting with a morning coffee looking at the lake. The location is so beautiful and tranquil we didn't want to go anywhere else. Using the provided kayaks on the lake followed by a soak in the hot tub was amazing. I highly recommend a stay here & will be back in the future.
Guest favorite
Cottage in Bellport
5 out of 5 average rating, 9 reviews

Bellport Inn, Charming Cottage in the Village!

JessicaRating, 5 stars11 months ago
Ivana and John are the most wonderful hosts! This was truly like staying at a family cottage and everything was just beautiful. John greeted us upon arrival and even had a bottle of wine for my husbands birthday! We loved staying here from the city because it was only a little over a hour to arrive and less than a hour to South Hampton where we had dinner. Also the little town is so so cute and we were able to walk over so quickly! We can’t wait to stay here again. Thank you again Ivana and John!
Guest favorite
Cottage in Fairfield
4.75 out of 5 average rating, 8 reviews

The Lil Nauti Cottage, Steps To Fairfield Beach

MarilynRating, 5 stars22 months ago
Lil Nauti was perfect for our family. The bedrooms were adequate, with very comfortable beds and plenty of pillows. The wardrobe space and drawers were great as we had a long stay with a lot of baggage! Jason has absolutely everything you could possibly want or need for a stay. The kitchen is really well equipped. Cute cottage and delightful private garden.

Pet-friendly cottage rentals

Guest favorite
Cottage in Greenwood Lake
4.93 out of 5 average rating, 188 reviews

Cozy home in the Village of Greenwood Lake

MichelineRating, 5 stars5 days ago
I love the fresh air flowing throughout this entire little cottage. Every room invites dappled sunlight filtered through lush summer foliage. It is truly cozy, whether enjoying a coffee on the back porch, journaling at the desk or chilling on the big comfy couch. Walk out the door and the lake and charming downtown are steps away. I find myself thinking I could truly spend a happy month, here. Stay. Return. I know I will.
Superhost
Cottage in Newtown
4.84 out of 5 average rating, 25 reviews

Streamside Cottage @ Sticks & Stones Farm

Yi ZengRating, 5 stars2 weeks ago
Hands-down one of the most beautiful airbnb I’ve ever had the fortune of staying at! Every detail - from the floor mat to the picnic basket to the window placement - was perfection. The little creek and vegetal labyrinth nearby was also such a treat. Heather and Chip were very responsive and flexible. The place is pretty conveniently located, with grocery shops and restaurants within a ten-minute drive, though I would recommend checking in before it gets too dark since the house is a little hard to find.
Guest favorite
Cottage in New Fairfield
4.97 out of 5 average rating, 36 reviews

Sunset Cabin Modern Home Kayak FirePit Lake Access

AlendaRating, 5 stars1 week ago
Great place that looked just like the pictures! We would definitely rent again. Brad always responded right away to my messages.
Guest favorite
Cottage in Norwalk
4.94 out of 5 average rating, 69 reviews

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

JudithRating, 5 stars1 month ago
The cottage is as pictured. Very clean with everything I needed. The area is beautiful for walking on the beach or the streets around the cottage. WiFi was strong throughout the cabin for working. Thanks Bert for your attention and listing this cottage.
Superhost
Cottage in Carmel Hamlet
4.83 out of 5 average rating, 160 reviews

Lake Cabin Escape–Fenced Yard+Firepit.Dogs welcome

ErinRating, 5 stars2 days ago
This place was wonderful. We were only there for a quick stay, and it was rainy, but that was ok because the cabin was so cute and cozy and fun. A bit of time sitting in the chairs out front in the morning with my coffee was exactly the quick weekend rejuvenation I needed. The cabin had everything we needed (and plenty of things we didn't need on this trip, but you might! I could see us playing board games or relaxing out on the back patio on a future trip.) A previous reviewer said this spot is what you expect an Airbnb to be, and that's exactly right. We picked it at first because it was convenient to a few Westchester things we needed to do, but we didn't want to drive home afterwards to CT on a summer Friday night. Spending this little bit of time in the Carmel area was genius because now we can't wait to go back there specifically for a real visit!
Guest favorite
Cottage in Putnam Valley
4.94 out of 5 average rating, 84 reviews

Cozy Retreat w/ Pool, Cinema Room & Fire Pit

DanielRating, 5 stars4 weeks ago
The house felt very homey, I stayed here with a total of five people including myself. We took advantage of the basement lounge space as well as the fire pit outside in the backyard. Overall, it’s an amazing getaway spot and I’d love to stay here again.
Top guest favorite
Cottage in Patchogue
4.94 out of 5 average rating, 239 reviews

Quaint Cottage on Long Island's South Shore.

JosephRating, 5 stars1 day ago
Highly recommend Leah's cottage. It worked very well for us as a weekend stay for our wedding night. She's one of the best hosts!
Guest favorite
Cottage in Milford
4.95 out of 5 average rating, 103 reviews

SILVER SANDS BEACH COTTAGE MILFORD NEAR YALE/TRAIN

OliviaRating, 5 stars1 month ago
A very cute and wonderful place to stay! Cozy, clean, private, and incredibly close to the beach! Lisa was extraordinarily understanding about the check-out time and process, would LOVE to stay again! :)

Private cottage rentals

Top guest favorite
Cottage in Rye
5 out of 5 average rating, 43 reviews

Rye Cottage - Walk to Beach & Playland

DominickRating, 5 stars3 weeks ago
This was a return stay for us. We were here at Donna and Bill's cottage last year and will be for all our future trips up north. They are kind, friendly and we always feel very welcomed. The Cottage is lovely, clean, a quiet location and close to major highways. couldn't ask for more ...Highly recommend The Cottage ....Thanks to Donna n Bill for having us!!!
Top guest favorite
Cottage in Putnam Valley
4.94 out of 5 average rating, 83 reviews

Peaceful Cottage with Grill | Walk to Lake

GaryRating, 5 stars2 months ago
This is a wonderful place. My wife and I loved it.
Guest favorite
Cottage in Putnam Valley
4.9 out of 5 average rating, 30 reviews

Hudson Valley Home 50 Min from NYC - dog friendly

EvanRating, 5 stars2 weeks ago
Really enjoyed our 1.5 month stay here. The place - while small - is cozy and has everything you'd need. Joanna does a great job making sure it's fully stocked (kitchen supplies, cleaning supplies, etc). The beds were comfy and the internet worked great. It's a very quiet space, in a nice little neighborhood, and the deck space is phenomenal (although it can get buggy!). We would definitely say again
Guest favorite
Cottage in Lordship
5 out of 5 average rating, 32 reviews

Waterfront Beach Cottage in Connecticut

PaulRating, 5 stars1 month ago
I grew up near here so I know just how magical it is. It did not disappoint with its beauty of LI sound. I also live in a cottage up the north end, and embrace all things others might seem quirky…. We loved them!! Amazing place!!
Superhost
Cottage in Fairfield
5 out of 5 average rating, 4 reviews

Peaceful & Bright Beach Cottage

AdamRating, 5 stars11 months ago
The proximity to the beach is unmatched. Additionally, a short drive or bike ride to Post Road provides an unlimited amount of food and culture to enjoy. The space is comfortable and clean with all you need for a short or long stay.
Guest favorite
Cottage in Brentwood
4.96 out of 5 average rating, 72 reviews

The Comfy Cottage

JanethRating, 5 stars1 week ago
Absolutely enjoyed my stay! Wanted a comfortable and peaceful place for my family and I and this was perfect! Extremely clean, cozy and had everything I needed. Definitely recommended this place!
Top guest favorite
Cottage in Westport
5 out of 5 average rating, 70 reviews

Wild Rose Cottage (Westport, CT)

NellRating, 5 stars1 week ago
We absolutely loved this little house. It's super-stylish, light and airy, clean and modern and a perfect place for a couple to stay. Mark is a very helpful and charming host - he came round to welcome us, when we arrived, and to tell us where the local restaurants & shops are. There are great facilities nearby - in particular a coffee shop which sells the most amazing freshly cooked donuts (which we very indulgently had for breakfast). The little house has everything you need for a very comfortable stay, and we highly recommend it.
Top guest favorite
Cottage in Black Rock
4.98 out of 5 average rating, 96 reviews

Spacious Cottage Loft

MauraRating, 5 stars6 months ago
Jim’s place was an absolute gem for my inaugural trip to Black Rock! The Loft is incredibly spacious and equipped with everything you could possibly need for a perfect stay. From the moment I arrived, I was impressed by the meticulous cleanliness, attention to detail, and beautiful furnishings. Jim's communication was top-notch, making the entire experience seamless. One of the highlights was the extensive music collection, perfect for setting the mood during my downtime. The bed and furniture provided a level of comfort that made it hard to leave. Nestled on a serene, tree-lined street, the location couldn’t be better; it’s just a leisurely stroll away from delightful restaurants, charming shops, food markets, and more. I can’t wait to return for another stay whenever I’m in the area!

Destinations to explore