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Browse Select New Canaan Vacation Homes

Captain's Cottage - Cold Spring Harbor Water Views

10.0 out of 10, Exceptional, (65)
"Great home to stay. Beautiful area to explore!"
The price is CA $524
CA $965 total
includes taxes & fees
Sep 8 - Sep 9
Captain's Cottage - Cold Spring Harbor Water Views

Stareway to Heaven Su

10.0 out of 10, Exceptional, (6)
"We stayed with family at this lovely home for my son’s graduation and Mother’s Day. The home is even nicer than the pictures- everything is top notch. It’s one block from a nice beach with lovely views from many of the rooms. We would love to come back and stay! "
Stareway to Heaven Su

Walk to Putnam Lake: Updated Home w/ Deck

Walk to Putnam Lake: Updated Home w/ Deck

Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!

10.0 out of 10, Exceptional, (44)
"Had an amazing stay. House was stocked with all of the essentials. Fantastic location. Would definitely stay again!"
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!

Charming 3-bedroom house with WiFi, AC in serene Fairfield

9.6 out of 10, Exceptional, (4)
"Thank you for the stay!"
Charming 3-bedroom house with WiFi, AC in serene Fairfield

Business or Weekend escape

9.2 out of 10, Wonderful, (44)
"Very nice owner with great communication. "
The price is CA $117
CA $202 total
includes taxes & fees
Aug 13 - Aug 14
Business or Weekend escape

Adorable Cottage with Water Views, Across the street from Prime & other eateries

9.8 out of 10, Exceptional, (63)
"This home had everything you could ask for. It was very cozy and the owner has put very thoughtful touches into the property. Would definitely stay again!"
Adorable Cottage with Water Views, Across the street from Prime & other eateries

Secluded Luxury Home – Peaceful, Comfortable, and Fully Private.

Secluded Luxury Home – Peaceful, Comfortable, and Fully Private.

Stay at Black Rock Harbor

10.0 out of 10, Exceptional, (21)
"Lovely home, responsive host & convenient location with water views. Cute & comfy decor with well appointed kitchen and off street parking. "
Stay at Black Rock Harbor

Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC

2.0 star property
10.0 out of 10, Exceptional, (5)
"We had a very nice family weekend. There was plenty of room, the furniture and beds were comfortable, and the kitchen had everything we needed. Great communication with the owner"
The price is CA $422
CA $882 total
includes taxes & fees
Aug 13 - Aug 14
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC

Quaint duplex with private yard. Walk to beach, dining, & shopping!

10.0 out of 10, Exceptional, (44)
"Needed a place to stay with our dog while visiting our granddaughters in a nearby town."
Quaint duplex with private yard. Walk to beach, dining, & shopping!

Spacious 4-bedroom house in charming Rye with AC

The price is CA $276
CA $625 total
includes taxes & fees
Aug 13 - Aug 14
Spacious 4-bedroom house in charming Rye with AC

Soothing Carriage House with Hot Tub in charming Stratford

10.0 out of 10, Exceptional, (2)
"John was a wonderful Host.We had a very relaxing time in the Hot Tub and the carriage house had everything we needed for our stay.We will definitely book again,Lisa and Holly"
Soothing Carriage House with Hot Tub in charming Stratford

St Julian's Place - Large updated Apt @ 40 Min NYC

10.0 out of 10, Exceptional, (35)
"Loved everything about this place! Plenty of space for everyone, great location four minutes from the commuter train, having offstreet parking was a huge blessing! So much good I could say about this property, communication was wonderful, and having a laundromat just steps down the street was perfect for a laundry refresh in our trip! The neighborhood is quiet yet close to everything and well kept!"
St Julian's Place - Large updated Apt @ 40 Min NYC

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (31)
"House was perfect for what we needed. Great proximity to the Amphitheater and Seaside Park. "
Cheerful 4 bedrooms residential house.

Lakeside luxury: beautiful, relaxing 4 bedroom home

10.0 out of 10, Exceptional, (28)
"This property was perfect for our needs! Checking in and out was simple and easy. The house is spacious and backyard is gorgeous! "
Lakeside luxury: beautiful, relaxing 4 bedroom home

Charming 2-bedroom house with WiFi, AC in Fairfield

8.0 out of 10, Very good, (3)
"Amalfi’s place was as described. It was clean and comfortable and mostly quiet. Amalfi was excellent with communication. Would certainly stay again when visiting family."
The price is CA $204
CA $474 total
includes taxes & fees
Aug 24 - Aug 25
Charming 2-bedroom house with WiFi, AC in Fairfield

Glen Cove Home: Walk to Boardwalk + Dining!

9.0 out of 10, Wonderful, (20)
"Quiet and comfortable house. Had all the amenities.Parking was a bonus"
Glen Cove Home: Walk to Boardwalk + Dining!

NEW Candlewood Lake 3BR 2BA Direct Waterfront Home~ Dock~Fire Pit~Sunset Views!

10.0 out of 10, Exceptional, (10)
"We had a wonderful vacation with our grandchildren and family. The children lived in the water if not kayaking or water boards they were fishing!! Rainy days puzzles were our entertainment the summer house provided everything one wanted or needed. It was a very delightful vacation"
NEW Candlewood Lake 3BR 2BA Direct Waterfront Home~ Dock~Fire Pit~Sunset Views!

Main Street Westport, walk to shops, dining, downtown

9.0 out of 10, Wonderful, (2)
"Beautiful home, great location, communicative hosts…A"
Main Street Westport, walk to shops, dining, downtown
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