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Cottages in Fairfield County

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Check prices for these dates

In two weeks
11 Sep - 13 Sep
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Top Cities in Fairfield County

A nighttime cityscape with illuminated buildings and a river.
CottagesCottages

Bridgeport

Bridgeport

Our top choices for Fairfield County cottages

Property grounds

1. Cozy 2-bedroom cottage in peaceful Danbury with AC

Cozy 2-bedroom cottage in peaceful Danbury with AC
Danbury
10.0 out of 10, Exceptional, (1 review)
"We were in town for Christmas with the family. The house was a perfect fit for us and the host responded almost immediately whenever we reached out to him. The house looks like a new renovation, and they did not skimp on finishings - very well done. It was very cold outside, but nice and warm inside. The snow didn’t slow us down. Great spot, will have to come back in the summer to enjoy the lake. Highly recommended! Thanks for letting us stay!!"
United States
Thomas H. H.
Cozy 2-bedroom cottage in peaceful Danbury with AC
Property grounds

2. Westport "Gold Coast" across from Southport beach

Westport "Gold Coast" across from Southport beach
Fairfield
10.0 out of 10, Exceptional, (103 reviews)
"Everything was wonderful, love staying there. "
United States
Shelley M.
Westport "Gold Coast" across from Southport beach
Exterior

3. Nama-stay, sweet pink Saugatuck Shores beach cottage

Nama-stay, sweet pink Saugatuck Shores beach cottage
Westport
9.2 out of 10, Wonderful, (17 reviews)
"Great fenced in yard for our pup"
United States
Deb S.
The price is AED 1,653
AED 2,780 total
includes taxes & fees
23 Sep - 24 Sep
Nama-stay, sweet pink Saugatuck Shores beach cottage
Property grounds

4. Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC

Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC
Greenwich
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful and restful"
United States
Lisa H.
The price is AED 2,959
AED 5,868 total
includes taxes & fees
31 Aug - 1 Sep
Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC
Exterior

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

Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?
Weston
10.0 out of 10, Exceptional, (16 reviews)
"Wonderful stay!"
United States
james v.
Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?
Outdoor spa tub

6. Great Fall pricing! Magical Views & Peaceful Vibes; private dock, kayaks, firepit, office!

Great Fall pricing! Magical Views & Peaceful Vibes; private dock, kayaks, firepit, office!
Newtown
8.8 out of 10, Excellent, (5 reviews)
"Charming cabin, great location… comfy and cozy"
United States
MaryJane B.
Great Fall pricing! Magical Views & Peaceful Vibes; private dock, kayaks, firepit, office!
Smart TV, fireplace, books, computer monitors

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

Tranquil 1 bedroom cottage with King size bed & Fireplace in charming Bethel, CT
Bethel
10.0 out of 10, Exceptional, (16 reviews)
"We loved our stay here! It was beautifully decorated and fully stocked with everything and more you would ever need. So quiet and serene! Located close to many things even tho you felt tucked away! Erica has a wonderful 1 bedroom cottage that I would highly recommend to anyone for a short stay or even a longer stay! Very comfortable!"
United States
Maryann
Tranquil 1 bedroom cottage with King size bed & Fireplace in charming Bethel, CT
Property grounds

8. Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!

Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
New Canaan
10.0 out of 10, Exceptional, (7 reviews)
"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."
United States
danyelle s.
The price is AED 1,466
AED 3,794 total
includes taxes & fees
24 Sep - 25 Sep
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
Exterior

9. Cozy Lake Community Cottage with private beach & hot tub - ideal for long stays

Cozy Lake Community Cottage with private beach & hot tub - ideal for long stays
New Fairfield
10.0 out of 10, Exceptional, (3 reviews)
"Lovely little 2/2 house in a great location with just about everything we needed. Very quiet too. Our host, Jonathan was very responsive when we had questions or concerns. We would highly recommend!"
United States
Mary Anne O.
Cozy Lake Community Cottage with private beach & hot tub - ideal for long stays
Shower, hair dryer, towels, soap

10. Squantz Pond Oasis, charming cottage, Firepit and lake view

Squantz Pond Oasis, charming cottage, Firepit and lake view
New Fairfield
Squantz Pond Oasis, charming cottage, Firepit and lake view
Coffee/tea maker, fridge, microwave, oven

11. Stylish Loft with Parking Near NYC + Hospital

Stylish Loft with Parking Near NYC + Hospital
West Side
9.6 out of 10, Exceptional, (17 reviews)
"Comfortable property, welcoming and flexible hosts."
United States
Kirk P.
Stylish Loft with Parking Near NYC + Hospital
Property grounds

12. Waterfront 1-bedroom cottage with dock in charming Fairfield

Waterfront 1-bedroom cottage with dock in charming Fairfield
Fairfield Beach
8.0 out of 10, Very Good, (2 reviews)
"The pictures do not do this cute little cottage justice. The entire front room is open with a lovely kitchen and a total wall of ever changing water views. I worked at a table in that room and watched the water all day. It is a birders paradise. This is a beach front community with multi million dollar properties. Lovely to walk around or bike but the area is also very quiet. And then there is Saw Creek and the lovely dock area outside. Great place if you have a boat, or Kayak but mind the...
United States
Dorrie J.
Waterfront 1-bedroom cottage with dock in charming Fairfield
Property grounds

13. Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC

Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC
Sherman
10.0 out of 10, Exceptional, (9 reviews)
"It was a wonderful place! Would definitely stay there again."
United States
SaSa W.
Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC
Exterior

14. Charming Fairfield Beach Cottage

Charming Fairfield Beach Cottage
Fairfield Beach
10.0 out of 10, Exceptional, (36 reviews)
"Overall a very smooth and enjoyable experience. "
United States
Dora M.
Charming Fairfield Beach Cottage
Exterior

15. Cos Cob Cottage- Full Kitchen, Pet Friendly

Cos Cob Cottage- Full Kitchen, Pet Friendly
Greenwich
9.6 out of 10, Exceptional, (5 reviews)
"Great Property. Driveway parking a bit of a challenge"
United States
Janet L.
Cos Cob Cottage- Full Kitchen, Pet Friendly
Exterior

16. Charming Studio-Cottage with WiFi & TV free parking in Greenwich

Charming Studio-Cottage with WiFi & TV free parking in Greenwich
Greenwich
Charming Studio-Cottage with WiFi & TV free parking in Greenwich
Terrace/patio

17. Pet-Friendly Cottage, 2 Mi to Saugatuck Falls

Pet-Friendly Cottage, 2 Mi to Saugatuck Falls
Redding
8.0 out of 10, Very Good, (3 reviews)
"Host was very communicative and helpful. "
United States
Jaclyn N.
Pet-Friendly Cottage, 2 Mi to Saugatuck Falls
Cottage (1 Bedroom) | Interior

18. Pet-friendly Cottage, 2 Mi to Saugatuck Falls

Pet-friendly Cottage, 2 Mi to Saugatuck Falls
3.0 star property
Redding
Pet-friendly Cottage, 2 Mi to Saugatuck Falls
Terrace/patio

19. Tranquility Between A Lake & Pond

Tranquility Between A Lake & Pond
New Fairfield
Tranquility Between A Lake & Pond
House (4 Bedrooms) | Interior

20. Family Home Near Roosevelt Forest & Historic Sites

Family Home Near Roosevelt Forest & Historic Sites
3.0 star property
Stratford
8.0 out of 10, Very Good, (1 review)
Family Home Near Roosevelt Forest & Historic Sites
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 Fairfield County Hotel Reviews

The Watershed

The Watershed

10/10 Excellent
"Such a chic hotel just an hour out of NY and directly off the Merritt Pkwy. Great Italian restaurant at the property. Staff were friendly and helpful. Will stay again when I’m headed into the city."
Rachael 1-night trip
Posted 6 hours ago
The Watershed

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