Search Old Greenwich Cottage Rentals from CA $319

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Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

Our top choices for Old Greenwich cottages

A deck with wicker furniture overlooking a river.

1. Historic, private riverfront cottage in peaceful Greenwich

Historic, private riverfront cottage in peaceful Greenwich
Greenwich
The price is CA $319
CA $518 total
includes taxes & fees
Nov 23 - Nov 24
Historic, private riverfront cottage in peaceful Greenwich
A wooden house with a stone pathway leading to a wooden deck.

2. 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, (14 reviews)
"Beautiful and restful"
United States
Lisa H.
The price is CA $1,137
CA $2,146 total
includes taxes & fees
Nov 12 - Nov 13
Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC
A two-story house with a white picket fence, a garage, and a tree in front.

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

Nama-stay, sweet pink Saugatuck Shores beach cottage
Westport
9.4 out of 10, Exceptional, (19 reviews)
"A sweet get away for which the highlights included a breezy screened porch and sensational walks right from the property. Easy shopping and neighbors right out of central casting who provided additional restaurant suggestions and general warmth. Would stay here again in a heart beat. We were here for a week and were sad to leave."
United States
Mel O.
Nama-stay, sweet pink Saugatuck Shores beach cottage
A wooden deck with a railing overlooking a well-maintained lawn and trees.

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

Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
New Canaan
9.8 out of 10, Exceptional, (11 reviews)
"Beautiful setting, and plenty of room for a family of four. Accommodations were very clean and spacious. Thank you for hosting us!"
United States
Susan K.
The price is CA $443
CA $944 total
includes taxes & fees
Nov 29 - Nov 30
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
A wooden deck with a railing overlooking a body of water and trees.

5. Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.

Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
Croton-on-Hudson
9.6 out of 10, Exceptional, (28 reviews)
"A lovely spot, very nice accommodations.Breakfast supples thoughtfully supplied as well as champagne to enjoy. "
United States
Eva C.
The price is CA $353
CA $570 total
includes taxes & fees
Nov 12 - Nov 13
Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
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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Learn more about Old Greenwich

Spend sunny afternoons at Tod's Point Beach where locals gather for swimming and spectacular Long Island Sound views. Explore the charming village centre with its independent shops, then head to nearby Greenwich Point Park for scenic coastal trails.

See all hotels in Old Greenwich
A calm lake with reflections of trees and a stone structure on the right.

Top reviews in Old Greenwich

A modern hotel with a prominent corner location, featuring a large entrance, a parking lot, and a landscaped area with illuminated plants.
The Lloyd Stamford, Tapestry Collection by Hilton

The Lloyd Stamford, Tapestry Collection by Hilton

The Lloyd Stamford, Tapestry Collection by Hilton
Downtown Stamford

10/10 Excellent

A wonderful place to stay! Great location within walking distance of dining and shopping. The room was very comfortable.
Canada
Michelle
Reviewed May 25, 2026
The Lloyd Stamford, Tapestry Collection by Hilton

Frequently Asked Questions

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What is there to do in Old Greenwich near my cottage?

The perfect travel accessory is a well-planned itinerary. Greenwich Point Park is a terrific place to kick off your exploration of Old Greenwich.

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