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Greenwich Holiday Rentals

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Our top choices for Greenwich holiday rentals

1. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (179 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
The price is NZ$339
includes taxes & fees
29 Sept - 30 Sept
Stamford Suites

2. Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Waterside
9.8 out of 10, Exceptional, (19 reviews)
"Very nice location, easy check in and check out. Also very comfortable."
United States
Leslie S.
The price is NZ$597
includes taxes & fees
20 Sept - 21 Sept
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

3. Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Port Chester
10.0 out of 10, Exceptional, (33 reviews)
"Exactly as described, comfy and close to the Capital and restaurants. We would definitely stay here again.Directions and parking instructions were very clear and helpful."
United States
Sarah W.
The price is NZ$715
includes taxes & fees
20 Sept - 21 Sept
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

4. Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich

Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Greenwich
8.0 out of 10, Very good, (5 reviews)
"This was a warm and inviting space. CC even offered me breakfast. I was a single woman in for a class reunion and had be somewhere on Sat and Sunday mornings. It was lovely coming back to relax and read. The space is small perfect for a couple with a young person. The patio over looks the river. The house is on a cul-de-sac perfect for strolling around the neighborhood. Very quiet and safe. Well lit path at night to the back, private entrance. Small fridge but holds a lot. Microwave, kurgurg...
United States
Kathleen W.
The price is NZ$388
includes taxes & fees
28 Sept - 29 Sept
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich

5. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.8 out of 10, Exceptional, (42 reviews)
"Nice stay"
United States
Christopher J.
The price is NZ$576
includes taxes & fees
5 Oct - 6 Oct
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

6. Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Downtown Stamford
9.2 out of 10, Wonderful, (11 reviews)
"loved walking the city. pizza was good."
United States
michelle b.
The price is NZ$576
includes taxes & fees
4 Oct - 5 Oct
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

7. Modern Luxe 1BR Apt in Downtown Stamford

Modern Luxe 1BR Apt in Downtown Stamford
Downtown Stamford
9.6 out of 10, Exceptional, (5 reviews)
"Our family stayed in the hotel(s) next door. It was so nice to have our own personal space!"
United States
Jill G.
The price is NZ$725
includes taxes & fees
20 Sept - 21 Sept
Modern Luxe 1BR Apt in Downtown Stamford

8. Romantic Hide Out

Romantic Hide Out
Waterside
3.0 out of 10, (2 reviews)
"Check-in was at 3 PM and I was unable to reach the host until 11 PM that night to gain access to the property. They never sent anything in advance. It was the most miserable experience I have ever had."
United States
Cheryl H.
The price is NZ$440
includes taxes & fees
20 Oct - 21 Oct
Romantic Hide Out

9. 2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.5 star property
Greenwich
The price is NZ$882
includes taxes & fees
30 Sept - 1 Oct
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

10. Modern Luxury 1BR Stamford Getaway

Modern Luxury 1BR Stamford Getaway
Downtown Stamford
8.0 out of 10, Very good, (2 reviews)
"The apartment is located in the hub bub of Stamford, a nice area very populated even in the evening where it feels safe. Apartment had all amenities that I needed. The host provided extra touches like a Keurig coffee pot stocked with Keurig cups and sugar. A washing machine and dryer were a plus as I like to pack only clean clothes. Bed was super comfortable. Modern design has a Zen vibe, great to decompress after travel. TV offered free movies that didn’t require my own subscription which...
United States
Debbie N.
Modern Luxury 1BR Stamford Getaway

11. Seabreeze at the beach west beach Stamford ct.

Seabreeze at the beach west beach Stamford ct.
Cove - East Side - Shippan
10.0 out of 10, Exceptional, (16 reviews)
"Fantastic place Very clean, a perfect stay !!!"
United States
bill J.
The price is NZ$951
includes taxes & fees
30 Sept - 1 Oct
Seabreeze at the beach west beach Stamford ct.

12. 2 Mi to NYC Train: WFH-Friendly Greenwich Apt!

2 Mi to NYC Train: WFH-Friendly Greenwich Apt!
Greenwich
8.0 out of 10, Very good, (4 reviews)
"Price was right for the stay! I would come back"
United States
Mark
The price is NZ$881
includes taxes & fees
30 Sept - 1 Oct
2 Mi to NYC Train: WFH-Friendly Greenwich Apt!

13. Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
New Rochelle
9.8 out of 10, Exceptional, (10 reviews)
"Host was very polite and helpful. Excellent condition VRBO."
United States
Drew C.
The price is NZ$598
includes taxes & fees
5 Oct - 6 Oct
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

14. Stylish Home and Cozy200

Stylish Home and Cozy200
Downtown Stamford
The price is NZ$616
includes taxes & fees
20 Oct - 21 Oct
Stylish Home and Cozy200

15. Solara – Luxury 1BR Downtown

Solara – Luxury 1BR Downtown
Downtown Stamford
The price is NZ$740
includes taxes & fees
15 Oct - 16 Oct
Solara – Luxury 1BR Downtown

16. 1 Queen Bed | Smoking

1 Queen Bed | Smoking
Elmsford
The price is NZ$248
includes taxes & fees
21 Sept - 22 Sept
1 Queen Bed | Smoking

17. Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"Friendly staff. Great room . Walking distance to the district theatre. Will def stay there again "
United States
Ronbert
The price is NZ$671
includes taxes & fees
20 Oct - 21 Oct
Guesthouse at Norwalk Inn

18. Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard

Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard
West Side
9.4 out of 10, Exceptional, (8 reviews)
"Place was clean, organized. A little odd to find but there was parking, the location felt safe. Would stay again."
United States
Dave J.
The price is NZ$1,343
includes taxes & fees
23 Sept - 24 Sept
Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard

19. Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
2.0 out of 10, (1 review)
The price is NZ$617
includes taxes & fees
30 Sept - 1 Oct
Elegant Hideaway with Free Parking

20. Spacious Stamford Home | Family, Work, Parking

Spacious Stamford Home | Family, Work, Parking
Cove - East Side - Shippan
8.6 out of 10, Excellent, (9 reviews)
"the home was nice clean if in the area I would stay here again"
United States
james w.
The price is NZ$944
includes taxes & fees
20 Sept - 21 Sept
Spacious Stamford Home | Family, Work, Parking
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 Greenwich Hotel Reviews

Find out more about Greenwich

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Greenwich holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Greenwich. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Greenwich. Seeing all the best attractions is bound to make you fall in love with Greenwich. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Greenwich short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Greenwich?

Yes, there are holiday rentals in Greenwich close to Bruce Museum of Arts and Science, or you can select a more secluded option if you're looking for a relaxing stay. The waterfront and restaurants are several reasons why visitors like Greenwich. Make sure you have time to check out the churches while you're in the area.

What are some of the best holiday rentals that Greenwich has to offer?

Spacious 5-bedroom house in enjoyable Brooklyn: This holiday home rental outside of Greenwich has air conditioning and free WiFi to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Greenwich?

Expedia has 12 holiday rentals for your stay in Greenwich.

What can I see and do in Greenwich?

Cultural attractions include Bruce Museum of Arts and Science and Flinn Gallery at Greenwich Library, whereas Hawthorne Beach and Wild Flower Sanctuary are a couple of picturesque spots to enjoy the outdoors. Greenwich Avenue and Putnam Cottage are other places to visit while you're in town.

What are holiday rentals like in Greenwich?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Greenwich. Holiday rentals feature extras such as WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for families.