Greenwich pickleball Stays, Resort Rentals, & Homes
Villa
10.0Exceptional
(28 Reviews)
3 Bedrooms
3 Baths
6 Guests
Private Pool
Parking
Pool
Ocean View
US $611/Night
7 Nights - US $4,277
Resort
- Holetown
- ·
- Sunset Crest
- 0.26 mi to center
7.3Very Good
(168 Reviews)
7 Baths
15 Guests
429.02 ft²
- Parking
- Pool
Spa
Balcony/Terrace
US $406/Night
7 Nights - US $2,845
Villa
- St. James
- ·
- Orange Hill
- 0.46 mi to center
10.0Exceptional
(5 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Private Pool
Breakfast- Parking
- Pool
US $1,127/Night
7 Nights - US $7,891
House
- St. James
- ·
- Westmoreland
- 0.26 mi to center
10.0Exceptional
(1 Review)
5 Bedrooms
6 Baths
10 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $1,909/Night
7 Nights - US $13,365
Villa
10.0Exceptional
(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
1582.29 ft²
- Parking
- Pool
- Balcony/Terrace
View
US $540/Night
7 Nights - US $3,777
Villa
- Holetown
- ·
- Sandy Lane
- 0.07 mi to center
9.8Exceptional
(17 Reviews)
9 Bedrooms
9 Baths
18 Guests
11000 ft²
- Private Pool
Hot Tub- Breakfast
- Parking
US $2,284/Night
7 Nights - US $15,987
Villa
- St. James
- ·
- Westmoreland
- 0.35 mi to center
9.6Exceptional
(10 Reviews)
3 Bedrooms
3 Baths
6 Guests
3830 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $690/Night
7 Nights - US $4,830
Cottage
- Holetown
- ·
- Sunset Crest
- 0.08 mi to center
9.2Exceptional
(50 Reviews)
3 Bedrooms
2 Baths
6 Guests
1722 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $248/Night
7 Nights - US $1,737
Villa
- St. James
- ·
- Westmoreland
- 0.48 mi to center
7 Bedrooms
7 Baths
14 Guests
7000 ft²
- Private Pool
- Pool
- Balcony/Terrace
Kitchen
US $4,994/Night
7 Nights - US $34,959
Luxury Places to Stay in Greenwich
Over 3171+ Luxury Places to Stay in or Near Greenwich
Villa
7 Bedrooms
8 Baths
14 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $4,577/Night
7 Nights - US $32,036
Villa
- Holetown
- ·
- Sandy Lane
- 0.12 mi to center
9 Bedrooms
9 Baths
18 Guests
10000 ft²
- Private Pool
- Hot Tub
- Pool
- Ocean View
US $4,398/Night
7 Nights - US $30,785
House
- St. James
- ·
- Westmoreland
- 0.29 mi to center
6 Bedrooms
8 Baths
12 Guests
- Private Pool
- Breakfast
- Parking
- Pool
US $3,294/Night
7 Nights - US $23,059
New
House
- Holetown
- ·
- Sandy Lane
- 0.34 mi to center
10 Bedrooms
9 Baths
16 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $3,242/Night
7 Nights - US $22,695
New
Villa
- St. James
- ·
- Westmoreland
- 0.48 mi to center
4 Bedrooms
5 Baths
8 Guests
7000 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $3,079/Night
7 Nights - US $21,554
Villa
- St. James
- ·
- Westmoreland
- 0.21 mi to center
4 Bedrooms
4 Baths
8 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $1,664/Night
7 Nights - US $11,648
Villa
- St. James
- ·
- Westmoreland
- 0.50 mi to center
3 Bedrooms
3 Baths
6 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $1,612/Night
7 Nights - US $11,284
Villa
4 Bedrooms
4 Baths
8 Guests
3173 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $1,185/Night
7 Nights - US $8,298
Villa
- St. James
- ·
- Westmoreland
- 0.35 mi to center
4 Bedrooms
5 Baths
8 Guests
Air Conditioner
Internet
Child Friendly
Laundry
US $957/Night
7 Nights - US $6,699
Top-Rated Villas with a Pool in Greenwich
Over 2276+ Top-Rated Private Villas with a Pool in or Near Greenwich
Villa
- St. James
- ·
- Westmoreland
- 0.30 mi to center
3 Bedrooms
3 Baths
6 Guests
2917 ft²
- Parking
- Pool
- Ocean View
- View
US $809/Night
7 Nights - US $5,664
House
- St. James
- ·
- Westmoreland
- 0.32 mi to center
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $723/Night
7 Nights - US $5,064
House
- St. Peter
- ·
- Merlin Bay
- 0.76 mi to center
4 Bedrooms
3 Baths
8 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $720/Night
7 Nights - US $5,038
House
- St. James
- ·
- Westmoreland
- 0.50 mi to center
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $651/Night
7 Nights - US $4,557
House
10.0Exceptional
(127 Reviews)
4 Bedrooms
4 Baths
8 Guests
2000 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $649/Night
7 Nights - US $4,540
Villa
10.0Exceptional
(112 Reviews)
4 Bedrooms
5 Baths
8 Guests
3444 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $485/Night
7 Nights - US $3,395
Villa
- Holetown
- ·
- Sunset Crest
- 0.23 mi to center
10.0Exceptional
(105 Reviews)
4 Bedrooms
4 Baths
8 Guests
2400 ft²
- Private Pool
Oceanfront- Parking
- Pool
US $986/Night
7 Nights - US $6,902
House
10.0Exceptional
(99 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Breakfast
- Parking
- Pool
- Ocean View
US $355/Night
7 Nights - US $2,485
House
10.0Exceptional
(71 Reviews)
4 Bedrooms
3 Baths
8 Guests
- Private Pool
- Breakfast
- Parking
- Pool
US $591/Night
7 Nights - US $4,138
Pet-Friendly Villas in Greenwich
Over 73+ Pet-Friendly Private Villas in or Near Greenwich
New
Apartment
- St. Thomas
- ·
- Christie
- 0.65 mi to center
10.0Exceptional
(6 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $123/Night
7 Nights - US $858
Apartment
- Holetown
- ·
- Sandy Lane
- 0.27 mi to center
9.4Exceptional
(14 Reviews)
1 Bedroom
1 Bath
2 Guests
204.51 ft²
- Parking
- Pool
- Balcony/Terrace
- View
US $150/Night
7 Nights - US $1,050
Apartment
- Holetown
- ·
- Sandy Lane
- 0.29 mi to center
10.0Exceptional
(5 Reviews)
1 Bedroom
1 Bath
2 Guests
205 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $128/Night
7 Nights - US $893
Villa
- St. James
- ·
- Westmoreland
- 0.32 mi to center
9.0Exceptional
(6 Reviews)
4 Bedrooms
2 Baths
8 Guests
3498.27 ft²
- Parking
- Pool
- Balcony/Terrace
- View
US $358/Night
7 Nights - US $2,506
Villa
- Rock Dundo
- ·
- Bakers Woods
- 0.06 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $728/Night
7 Nights - US $5,095
House
10.0Exceptional
(2 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $431/Night
7 Nights - US $3,018
New
Villa
- Holetown
- ·
- Sandy Lane
- 0.08 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
3 Baths
8 Guests
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
US $972/Night
7 Nights - US $6,804
House
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $381/Night
7 Nights - US $2,670
Apartment
8.0Excellent
(1 Review)
2 Bedrooms
1 Bath
3 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $191/Night
7 Nights - US $1,334
Large Private Villas in Greenwich
Over 1727+ Large Villas in or Near Greenwich for Groups and Families
New
Villa
4 Bedrooms
3 Baths
8 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $747/Night
7 Nights - US $5,226
Villa
10.0Exceptional
(2 Reviews)
3 Bedrooms
3 Baths
6 Guests
1819.1 ft²
Private Beach- Parking
- Pool
- Ocean View
US $1,171/Night
7 Nights - US $8,197
Villa
- St. James
- ·
- Westmoreland
- 0.33 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
- Private Pool
- Parking
- Pool
- Ocean View
US $792/Night
7 Nights - US $5,544
Villa
3 Bedrooms
3 Baths
6 Guests
- Kitchen
- Internet
- Child Friendly
- Laundry
US $505/Night
7 Nights - US $3,535
Villa
10.0Exceptional
(2 Reviews)
3 Bedrooms
3 Baths
4 Guests
3390.63 ft²
- Parking
- Pool
- View
- Air Conditioner
US $505/Night
7 Nights - US $3,535
Villa
10.0Exceptional
(53 Reviews)
4 Bedrooms
3 Baths
8 Guests
3750 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $753/Night
7 Nights - US $5,269
Villa
10.0Exceptional
(43 Reviews)
2 Bedrooms
2 Baths
5 Guests
1798 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $550/Night
7 Nights - US $3,853
Villa
- Holetown
- ·
- Mount Standfast
- 0.26 mi to center
10.0Exceptional
(37 Reviews)
4 Bedrooms
4 Baths
8 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $732/Night
7 Nights - US $5,121
Villa
10.0Exceptional
(30 Reviews)
2 Bedrooms
2 Baths
4 Guests
990 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $272/Night
7 Nights - US $1,907
Wheelchair Accessible Holiday Homes in Greenwich
Over 228+ Wheelchair Accessible Villas and Holiday Homes in or Near Greenwich
Apartment
10.0Exceptional
(52 Reviews)
3 Bedrooms
2 Baths
6 Guests
1817 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $718/Night
7 Nights - US $5,023
Apartment
9.4Exceptional
(18 Reviews)
16 Bedrooms
10 Baths
32 Guests
1773.35 ft²
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $625/Night
7 Nights - US $4,373
Apartment
- St. James
- ·
- Old Trees Bay
- 0.15 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $762/Night
7 Nights - US $5,334
Condo
- Holetown
- ·
- Sunset Crest
- 0.17 mi to center
10.0Exceptional
(51 Reviews)
1 Bedroom
1 Bath
3 Guests
700 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $108/Night
7 Nights - US $759
Resort
- St. James
- ·
- Old Trees Bay
- 0.20 mi to center
8.6Fabulous
(10 Reviews)
1 Bath
14 Guests
547.17 ft²
- Oceanfront
- Hot Tub
- Breakfast
- Parking
US $1,142/Night
7 Nights - US $7,996
Apartment
- Holetown
- ·
- Sunset Crest
- 0.04 mi to center
10.0Exceptional
(47 Reviews)
1 Bedroom
1 Bath
2 Guests
750 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $135/Night
7 Nights - US $945
New
Apartment
- St. James
- ·
- Old Trees Bay
- 0.19 mi to center
10.0Exceptional
(28 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $535/Night
7 Nights - US $3,746
House
10.0Exceptional
(20 Reviews)
5 Bedrooms
5 Baths
10 Guests
6500 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $3,724/Night
7 Nights - US $26,067
Apartment
- Holetown
- ·
- Mount Standfast
- 0.28 mi to center
10.0Exceptional
(9 Reviews)
2 Bedrooms
1 Bath
4 Guests
1100 ft²
- Breakfast
- Parking
- Pool
- Ocean View
US $400/Night
7 Nights - US $2,797
Greenwich Villas, Airbnb and Holiday Homes Under $200
Over 271+ Greenwich Private Villas, Airbnb and Holiday Homes Under $200
Cottage
10.0Exceptional
(71 Reviews)
1 Bedroom
1 Bath
2 Guests
750 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $157/Night
7 Nights - US $1,098
Apartment
- Holetown
- ·
- Sunset Crest
- 0.17 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
699.65 ft²
- Parking
- Pool
- Balcony/Terrace
- View
US $170/Night
7 Nights - US $1,190
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
3 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $125/Night
7 Nights - US $875
Apartment
- Holetown
- ·
- Mount Standfast
- 0.29 mi to center
10.0Exceptional
(57 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $199/Night
7 Nights - US $1,396
Apartment
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
5 Guests
- Parking
- View
- Air Conditioner
- Internet
US $67/Night
7 Nights - US $469
House
- Paynes Bay
- ·
- Holder's Hill
- 0.34 mi to center
10.0Exceptional
(44 Reviews)
2 Bedrooms
2 Baths
4 Guests
1278 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $194/Night
7 Nights - US $1,359
Apartment
- Holetown
- ·
- Sunset Crest
- 0.09 mi to center
10.0Exceptional
(15 Reviews)
1 Bedroom
1 Bath
2 Guests
400 ft²
- Parking
- Pool
- Balcony/Terrace
- View
US $99/Night
7 Nights - US $692
Cottage
- Holetown
- ·
- Sunset Crest
- 0.04 mi to center
10.0Exceptional
(13 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $148/Night
7 Nights - US $1,039
Apartment
10.0Exceptional
(9 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $119/Night
7 Nights - US $835
Instantly Bookable Villa Rentals in Greenwich
Over 938+ Instantly Bookable Private Villas in or Near Greenwich
House
4 Bedrooms
5 Baths
8 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $824/Night
7 Nights - US $5,766
Apartment
2 Bedrooms
2 Baths
4 Guests
1550 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $434/Night
7 Nights - US $3,035
Apartment
- Holetown
- ·
- Mount Standfast
- 0.32 mi to center
10.0Exceptional
(44 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $407/Night
7 Nights - US $2,852
House
- Holetown
- ·
- Sandy Lane
- 0.21 mi to center
10.0Exceptional
(30 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $219/Night
7 Nights - US $1,536
House
- Holetown
- ·
- Sunset Crest
- 0.10 mi to center
10.0Exceptional
(26 Reviews)
4 Bedrooms
4 Baths
8 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $435/Night
7 Nights - US $3,046
House
- Holetown
- ·
- Sunset Crest
- 0.12 mi to center
10.0Exceptional
(24 Reviews)
4 Bedrooms
4 Baths
8 Guests
3900 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $779/Night
7 Nights - US $5,450
Condo
- Holetown
- ·
- Mount Standfast
- 0.28 mi to center
10.0Exceptional
(23 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $344/Night
7 Nights - US $2,407
House
- Holetown
- ·
- Sunset Crest
- 0.18 mi to center
10.0Exceptional
(22 Reviews)
3 Bedrooms
2 Baths
6 Guests
1330 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $461/Night
7 Nights - US $3,229
House
10.0Exceptional
(22 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $340/Night
7 Nights - US $2,383
Book a Last Minute Place to Stay in Greenwich
About Greenwich Vacation Rentals
Discover over 3180 amazing vacation rental options in Greenwich with pickleball courts or nearby facilities. From resorts to hotels, villas to condos, PickleTrip connects you with a vast selection of pickleball-ready amenities at great prices, providing you with the perfect spot to base your next pickleball vacation. Stay and Play pickleball When You Travel and uncover great stays in Greenwich.
Find exclusive last-minute deals on vacation rentals, resorts, and hotels with private courts and nearby facilities with PickleTrip™, whether you're traveling solo or with a group. Our platform offers a variety of stay options, from vacation rentals to Airbnb-style properties, all with private pickleball courts or nearby facilities. Compare options from multiple suppliers with a single click to find the perfect stay that fits your budget and style. Places to stay near pickleball courts are an average of 1723.07 ft², with prices averaging US $1,512 per night.
With PickleTrip™, you can easily search for and book your next pickleball vacation rental with courts or nearby facilities. Our platform connects you with the ideal holiday rental to create a lifetime of travel memories. Prices listed are often discounted versus rack rates, so you can secure your perfect place to stay today and get ready to play pickleball in Greenwich.
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Top Pickleball-Ready Accommodation Types in Greenwich
| Type | Count |
|---|---|
| Villas | 1550 |
| Vacation Homes | 783 |
| Holiday Apartments | 619 |
| Cottages | 27 |
Use these Quick Filters to Find a Vacation Rental in Greenwich
★ Pro Tip: PickleTrip™ is a travel platform, connecting avid pickleball players and enthusiasts with a variety of vacation rentals, resorts, and hotels featuring private pickleball courts or nearby facilities. We curate a vast selection of properties from trusted sources, providing you with unbeatable options and pricing to find the perfect pickleball getaway. Experience unforgettable pickleball matches in Greenwich with PickleTrip™.
Weather in Greenwich, BB
View the weather forecast for Greenwich before booking your Greenwich Vacation Rentals to confirm your best time to go.
December - February
High 85°F Low 73°F
March - May
High 86°F Low 69°F
June - August
High 88°F Low 74°F
September - November
High 89°F Low 75°F
Top Attractions Around Greenwich, BB
PickleTrip offers a large selection of top attractions around Greenwich . Research things to do on your vacation before you visit Greenwich.
Frequently Asked Questions About Greenwich?
What are the top vacation rentals, resorts, and hotels in Greenwich with Courts?
Experience the ultimate pickleball vacation with PickleTrip™. We offer a variety of premium rental properties, resorts, and hotels with private pickleball courts or nearby facilities in Greenwich. Whether you're a beginner or a seasoned player, we have the perfect destination for you to stay and play. Book now and discover the best pickleball vacation spots in Greenwich!
- Beautiful Barbados Villa - St James - with beach membership
- A Beautiful Royal Westmoreland Villa With A Private Pool And Beach Club Access
- #1 in Barbados! Sandy Lane Beach Estate w/50 Foot Pool, Pickleball Court! ★
- Villa with Pool and Golf Views - Villa Grove
- Only 3 mins walk to Beach and Beach Club
- The Club Barbados - All Inclusive - Adults Only
- Villa St. Lucy
- La Maison Michelle
- Bon Vivant
- Monkey Manor at Royal Westmoreland by Young Estates
How many pickleball-ready properties have private pools in Greenwich?
Discover 1402 accommodations with private or nearby pickleball courts in Greenwich. Some of the best destinations to stay and play pickleball are:
- 1 bedroom Beachfront Condo, small pool, gorgeous sea view
- Westmoreland Modern sea View Villa with pool
- Royal Westmoreland Benjoli Breeze by Island Villas
- The Summer House, Sugar Hill Resort | Ocean View - Located in Wonderful Sugar Hill with House Cleaning Included
Which vacation rentals, resorts, or hotels in Greenwich is best for families looking for a pickleball-getaway?
Looking for a fun and active getaway with pickleball courts in Greenwich? With PickleTrip™, you'll have access to a wide selection of top-rated properties that offer private pickleball courts or nearby facilities. Make the most of you getaway and ace your A-game while you travel.
- Sugar Hill, Stunning, 2 Bed 2 Bath Apartment, Pool, Beach Club, Tennis, Golf
- Jacks Place - by ZenBreak
- Kingsgate #1 - by Zenbreak
How many PickleTrip vacation rentals or resorts are available in Greenwich?
PickleTrip™ offers a diverse selection of properties with private pickleball courts or nearby facilities to enhance your pickleball experience on your next trip. With a combination of established great stays and new options in top locations, PickleTrip™ has over 3180 properties listed in Greenwich in 2026, and the number only continues to grow. By consolidating listings from various providers, PickleTrip™ brings you the best luxury stays for a sporty, professional, and fun travel experience.
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