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Aug 15 - Aug 17
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Browse Select New Canaan Cottages

South Salem Vacation Rental w/ Furnished Deck!
Fridge, microwave, stovetop, dishwasher

South Salem Vacation Rental w/ Furnished Deck!

10.0 out of 10, Exceptional, (2)
"This was the second time I stayed at this property and really do love it. It is close enough to my family in Ridgefield for me to fee like I am just around the corner, while being in a quiet, peaceful private property. The setup was perfect for myself and my mom, but could also accommodate a larger group. It isn’t a big space, but had everything that we needed. I would highly recommend this property and will definitely be looking to stay here again on another visit. Thank you!"
South Salem Vacation Rental w/ Furnished Deck!
Westport "Gold Coast" across from Southport beach
Property grounds

Westport "Gold Coast" across from Southport beach

10.0 out of 10, Exceptional, (91)
"Fantastic place, location with great host. Highly recommended "
Westport "Gold Coast" across from Southport beach
Waterfront Beautiful Fun Beach Cottage Sunsets Inspiring Peaceful 1hr NYC Wow
Terrace/patio

Waterfront Beautiful Fun Beach Cottage Sunsets Inspiring Peaceful 1hr NYC Wow

9.0 out of 10, Wonderful, (7)
"Very comfortable space & accomodating host! Fantastic views of Northport Harbour and steps away from the water's edge! Would return and strongly recommend."
Waterfront Beautiful Fun Beach Cottage Sunsets Inspiring Peaceful 1hr NYC Wow
Romantic retreat with stunning views of Croton River Gorge, a birder haven
Outdoor dining

Romantic retreat with stunning views of Croton River Gorge, a birder haven

9.8 out of 10, Exceptional, (6)
Romantic retreat with stunning views of Croton River Gorge, a birder haven
Second floor cottage apartment located in a private community.
Smart TV

Second floor cottage apartment located in a private community.

9.6 out of 10, Exceptional, (16)
"This was a great property - location was perfect and the hosts were so easy to communicate with. It was exactly as pictured and was a great stay!"
Second floor cottage apartment located in a private community.
Beach cottage on private beach!
Beach nearby, sun loungers, beach towels

Beach cottage on private beach!

10.0 out of 10, Exceptional, (4)
"It was a very nice cottage. Great price for staying right on the beach"
Beach cottage on private beach!
Walk to Beach: Luxe Home w/ Fire Pit in Rowayton!
House (3 Bedrooms) | Interior

Walk to Beach: Luxe Home w/ Fire Pit in Rowayton!

3.0 star property
Walk to Beach: Luxe Home w/ Fire Pit in Rowayton!
Adorable 1-Bedroom Cottage in Weston, CT
Fridge, microwave, oven, stovetop

Adorable 1-Bedroom Cottage in Weston, CT

10.0 out of 10, Exceptional, (42)
"Loved our stay. We'll be back I am sure."
The price is CA $268
CA $412 total
includes taxes & fees
Aug 31 - Sep 1
Adorable 1-Bedroom Cottage in Weston, CT
Lakefront Brewster Vacation Rental w/ Private Dock
TV, fireplace, books

Lakefront Brewster Vacation Rental w/ Private Dock

10.0 out of 10, Exceptional, (7)
"Felt relaxed from first step in the door! Wonderful view, comfortable beds, helpful management, great kitchen! Loved the heated tile floor in main bath! Lots of birds to enjoy with books and binoculars for identifying. "
Lakefront Brewster Vacation Rental w/ Private Dock
Hudson River Views + Firepit, Patio, Dog Run, Game Room Stone Manor
House (4 Bedrooms) | Interior

Hudson River Views + Firepit, Patio, Dog Run, Game Room Stone Manor

3.0 star property
Hudson River Views + Firepit, Patio, Dog Run, Game Room Stone Manor
Charming 2 Bedroom Cottage in Peaceful New Canaan
Property grounds

Charming 2 Bedroom Cottage in Peaceful New Canaan

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had a wonderful Christmas getaway with family at the “Ice Cream Cottage”. It is much more spacious than it looks on the outside.It was clean and had everything we needed. Host was attentive to any questions we had.The fenced in yard was great for our “fur baby” to run around."
Charming 2 Bedroom Cottage in Peaceful New Canaan
Beachfront cottage located in the heart of Fairfield Beach!!
On the beach

Beachfront cottage located in the heart of Fairfield Beach!!

9.6 out of 10, Exceptional, (15)
"I grew up here! Always fun"
Beachfront cottage located in the heart of Fairfield Beach!!
Trendy 1 bedroom +loft apartment w/ parking
Smart TV

Trendy 1 bedroom +loft apartment w/ parking

10.0 out of 10, Exceptional, (12)
"Perfect for my needs. Would stay again for sure"
Trendy 1 bedroom +loft apartment w/ parking
Beach house cottage steps to private beach in the heart of Bayville
Interior

Beach house cottage steps to private beach in the heart of Bayville

10.0 out of 10, Exceptional, (10)
"Great location. Very clean modern cottage by the sea. Would love to stay again. "
Beach house cottage steps to private beach in the heart of Bayville
Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?
Exterior

Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?

10.0 out of 10, Exceptional, (9)
"Wonderful stay!"
Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?
Charming Fairfield Beach 3BR 2BA Cottage By The Sea
Dining

Charming Fairfield Beach 3BR 2BA Cottage By The Sea

10.0 out of 10, Exceptional, (32)
"Gerard was very responsive and helpful and the rental was lovely and in a great location. The beach access was great as were the beach accessories we could borrow! The house stayed nice and cool in during the hot days! Would stay again."
Charming Fairfield Beach 3BR 2BA Cottage By The Sea
Tranquil 1 bedroom cottage with King size bed & Fireplace in charming Bethel, CT
Fridge, microwave, oven, stovetop

Tranquil 1 bedroom cottage with King size bed & Fireplace in charming Bethel, CT

10.0 out of 10, Exceptional, (7)
"Great relaxing stay quite and comfortable "
Tranquil 1 bedroom cottage with King size bed & Fireplace in charming Bethel, CT
Sun and Fun on the beach!!
Dining

Sun and Fun on the beach!!

9.6 out of 10, Exceptional, (16)
"Perfect beach and outdoor life for young kids! Such a great relaxing long weekend - the house had everything we needed. Hoping for another stay soon!"
Sun and Fun on the beach!!
Lakefront Brewster Vacation Rental w/ Private Dock
Cottage (3 Bedrooms) | Interior

Lakefront Brewster Vacation Rental w/ Private Dock

3.0 star property
Lakefront Brewster Vacation Rental w/ Private Dock
Historic Pound Ridge Cottage, 2 Beds, Fully Furnished
Smart TV, fireplace, computer monitors, printers

Historic Pound Ridge Cottage, 2 Beds, Fully Furnished

9.4 out of 10, Exceptional, (3)
"A cozy, well-maintained cottage, conveniently located near our son and his family who we were visiting. Modern appliances in the kitchen. Exterior and interior were as shown on VRBO. The property manager and owner were very helpful whenever we needed anything. Highly recommended. We would definitely like to stay here again whenever we visit our son."
Historic Pound Ridge Cottage, 2 Beds, Fully Furnished
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top New Canaan Hotel Reviews

The Circle Hotel Fairfield

The Circle Hotel Fairfield

10/10 Excellent
"This is my Go-To / First Choice when visiting the Fairfield area. Rooms are always clean & immaculate + very comfy bed, great towels, good size room...and traveling alone I feel safe! Staff is so welcoming and extra helpful. Keep it up."
Nancy 2-night trip
Posted 1 day ago
The Circle Hotel Fairfield