Old Greenwich Vacation Rentals from $162: Search Short-Term Rentals

Q: What are some of the best vacation rentals in Old Greenwich?

PureHeart House, Spacious, 3bdr30 MN from Manhattan. NYC : This vacation home rental near Old Greenwich is located next to a golf course and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like foosball.

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Our top choices for Old Greenwich vacation rentals

1. Stamford Suites

Downtown Stamford

Selena

$141 nightly

Aug 20 - Aug 21

Total with taxes and fees

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

Waterside

Sara C.

$335 nightly

Sep 8 - Sep 9

Total with taxes and fees

3. Modern Luxury 1BR Stamford Getaway

Downtown Stamford

"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...

Debbie N.

$319 nightly

Aug 17 - Aug 18

Total with taxes and fees

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

Downtown Stamford

michelle b.

$273 nightly

Aug 24 - Aug 25

Total with taxes and fees

5. Romantic Hide Out

Waterside

Cheryl H.

$230 nightly

Sep 14 - Sep 15

Total with taxes and fees

6. Modern Luxe 1BR Apt in Downtown Stamford

Downtown Stamford

Jill G.

$369 nightly

Aug 19 - Aug 20

Total with taxes and fees

7. 2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

Greenwich

$252 nightly

Aug 23 - Aug 24

Total with taxes and fees

Standard Room, 1 King Bed, Main Building | Property entrance

8. Guesthouse at Norwalk Inn

Historic District

Ronbert

$219 nightly

Aug 17 - Aug 18

Total with taxes and fees

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

Port Chester

Sarah W.

$352 nightly

Aug 18 - Aug 19

Total with taxes and fees

10. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Greenwich

Martina F.

$360 nightly

Sep 15 - Sep 16

Total with taxes and fees

Coffee/tea maker, fridge, microwave, oven

11. Stylish Home and Cozy200

Downtown Stamford

$227 nightly

Aug 17 - Aug 18

Total with taxes and fees

Classic Suite | Iron/ironing board, WiFi (free), bed sheets

12. DUNE Fairfield Beach

Fairfield Beach

Stacie

$233 nightly

Sep 13 - Sep 14

Total with taxes and fees

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

Greenwich

"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...

Kathleen W.

$202 nightly

Sep 4 - Sep 5

Total with taxes and fees

14. 2 Mi to NYC Train: WFH-Friendly Greenwich Apt!

Greenwich

Ann E.

$259 nightly

Aug 23 - Aug 24

Total with taxes and fees

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

West Side

Dave J.

$619 nightly

Sep 14 - Sep 15

Total with taxes and fees

16. Luxury NYC Home Game Room Free Parking

White Plains

"After flying in with four of us from Los Angeles on a Red Eye, we had to drive around for 4-5 hours until we were able to check in at 4pm, however after hours of trying to get into the property with no answer on the contact number ,we finally were able to have the local property manager come out and say that the property overbooked and had no room for us. I spent over 2 hours on the phone getting the run around by Expedia with mixed stories of our accommodations. FINALLY with now the story is...

Jorge

$355 nightly

Aug 19 - Aug 20

Total with taxes and fees

17. 5BR Beach House, Water Views, Game Room, Backyard

Cove - East Side - Shippan

Laura M.

$784 nightly

Aug 18 - Aug 19

Total with taxes and fees

18. Elegant Hideaway with Free Parking

White Plains

$308 nightly

Aug 18 - Aug 19

Total with taxes and fees

19. Elegant Home

Downtown Stamford

$268 nightly

Sep 15 - Sep 16

Total with taxes and fees

20. Modern Comforts ,Free Gym Access

Downtown Stamford

$227 nightly

Aug 17 - Aug 18

Total with taxes and fees

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Top Old Greenwich Hotel Reviews

Hotel Nyack, a JdV by Hyatt Hotel

10/10 Excellent

"Loved the food!!!! The staff was exceptionally welcoming and helpful! The rooms are decorated so beautifully. I loved the aesthetic of the whole hotel! The hit tub could’ve been warmer, but overall, it was a great experience."

Hyatt Regency Greenwich

10/10 Excellent

"This was our second stay, a year after our first one. The property is very clean. If you order room service, it is delivered right on time that it says it will be delivered. All staff appear genuinely friendly and helpful. The pool is wonderful. We even tried the movie theater this time and it was such a comfortable experience. This will continue to be my favorite place to go to when we come for our visit as a family!"

Hampton Inn White Plains/Tarrytown

8/10 Good

"Overall, everything was great. The property itself is clean, the breakfast buffet was pretty good, and the room for the most part was clean. The only issue really was with the bathtub. There were some areas not properly cleaned. Other than that, it was a fantastic sleep stop for our road trip."

Find out more about Old Greenwich

Everything you need to know about Old Greenwich vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Old Greenwich vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Old Greenwich vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Old Greenwich vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Old Greenwich. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Old Greenwich in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $162 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Old Greenwich rentals

At Expedia, we put the best Old Greenwich vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Old Greenwich rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Old Greenwich vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Old Greenwich. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Things to do in Stamford

Frequently asked questions

Can I find vacation rentals in Old Greenwich?

Yes, we offer vacation rentals close to well known points of interest in Old Greenwich, or you can go with a more remote option if you want a relaxing place to stay. Visitors like the top-notch restaurants and shops in Old Greenwich. Make sure you have time to check out the beaches and cafes during your trip.

What are some of the best vacation rentals in Old Greenwich?

PureHeart House, Spacious, 3bdr 30 MN from Manhattan. NYC: This vacation home rental near Old Greenwich is located next to a golf course and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like foosball.

How many vacation rentals will I find in Old Greenwich?

Expedia has 13 vacation rentals for your stay in Old Greenwich.

What can I see and do in Old Greenwich?

Greenwich Point Park and Rosa Hartman Park are a couple of lovely local spots to get outside and enjoy nature. Commerce Park and Dundee Woods are other places to visit while you're in town.

What are vacation rentals like in Old Greenwich?

Vacation rentals are privately owned accommodations you can reserve for a short or long stay in Old Greenwich. Vacation rentals provide amenities like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from shared hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a family trip.

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Check prices for these dates

Our top choices for Old Greenwich vacation rentals

1. Stamford Suites

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

3. Modern Luxury 1BR Stamford Getaway

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

5. Romantic Hide Out

6. Modern Luxe 1BR Apt in Downtown Stamford

7. 2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

8. Guesthouse at Norwalk Inn

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

10. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

11. Stylish Home and Cozy200

12. DUNE Fairfield Beach

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

14. 2 Mi to NYC Train: WFH-Friendly Greenwich Apt!

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

16. Luxury NYC Home Game Room Free Parking

17. 5BR Beach House, Water Views, Game Room, Backyard

18. Elegant Hideaway with Free Parking

19. Elegant Home

20. Modern Comforts ,Free Gym Access

Find vacation rentals that suit your style

Top Old Greenwich Hotel Reviews

Hotel Nyack, a JdV by Hyatt Hotel

Hyatt Regency Greenwich

Hampton Inn White Plains/Tarrytown

Hilton Long Island/Huntington

La Quinta Inn & Suites by Wyndham Stamford / New York City

Find out more about Old Greenwich

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