Greenwich Vacation Rentals & Ski-in/Ski-out Homes
House
10.0Exceptional
(127 Reviews)
4 Bedrooms
4 Baths
8 Guests
2000 ft²
Private Pool
Oceanfront
Parking
Pool
US $498/Night
7 Nights - US $3,487
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
- ·
- Orange Hill
- 0.46 mi to center
10.0Exceptional
(5 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Private Pool
- Oceanfront
Breakfast- Parking
US $1,127/Night
7 Nights - US $7,891
Villa
10.0Exceptional
(111 Reviews)
4 Bedrooms
5 Baths
8 Guests
3444 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $490/Night
7 Nights - US $3,432
House
10.0Exceptional
(2 Reviews)
4 Bedrooms
4 Baths
8 Guests
3498.27 ft²
- Parking
- Pool
Balcony/Terrace
View
US $520/Night
7 Nights - US $3,643
Villa
- Holetown
- ·
- Sunset Crest
- 0.23 mi to center
10.0Exceptional
(104 Reviews)
4 Bedrooms
4 Baths
8 Guests
2400 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $578/Night
7 Nights - US $4,048
House
10.0Exceptional
(99 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Breakfast
- Parking
- Pool
US $317/Night
7 Nights - US $2,218
House
10.0Exceptional
(78 Reviews)
2 Bedrooms
2 Baths
4 Guests
1800 ft²
- Private Pool
- Oceanfront
Hot Tub- Parking
US $351/Night
7 Nights - US $2,459
House
10.0Exceptional
(71 Reviews)
4 Bedrooms
3 Baths
8 Guests
- Private Pool
- Oceanfront
- Breakfast
- Parking
US $493/Night
7 Nights - US $3,454
Luxury Places to Stay in Greenwich
Over 3169+ Luxury Places to Stay in or Near Greenwich
Villa
- Holetown
- ·
- Sandy Lane
- 0.32 mi to center
12 Bedrooms
12 Baths
24 Guests
10559.4 ft²
- Private Pool
- Parking
- Pool
Air Conditioner
Unlock the Best Price
Villa
- Holetown
- ·
- Mount Standfast
- 0.17 mi to center
10 Bedrooms
10 Baths
20 Guests
- Private Pool
- Hot Tub
- Pool
- Ocean View
Unlock the Best Price
Villa
6 Bedrooms
6 Baths
12 Guests
10710.09 ft²
- Private Pool
- Parking
- Pool
- Air Conditioner
Unlock the Best Price
Villa
- Holetown
- ·
- Sunset Crest
- 0.17 mi to center
6 Bedrooms
6 Baths
12 Guests
8008 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
Unlock the Best Price
New
Villa
- St. James
- ·
- Old Trees Bay
- 0.17 mi to center
9 Bedrooms
9 Baths
20 Guests
9000 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
Unlock the Best Price
New
Villa
- St. James
- ·
- Old Trees Bay
- 0.17 mi to center
8 Bedrooms
9 Baths
18 Guests
9000 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
Unlock the Best Price
Villa
- Holetown
- ·
- Sunset Crest
- 0.19 mi to center
5 Bedrooms
5 Baths
10 Guests
13509 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
Unlock the Best Price
New
Villa
- St. James
- ·
- Old Trees Bay
- 0.17 mi to center
6 Bedrooms
7 Baths
14 Guests
9000 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
Unlock the Best Price
House
6 Bedrooms
6 Baths
12 Guests
- Air Conditioner
Internet
Child Friendly
Laundry
US $9,228/Night
7 Nights - US $64,599
Top-Rated Vacation Rentals with a Pool in Greenwich
Over 2191+ Top-Rated Vacation Rentals with a Pool in or Near Greenwich
Apartment
- Holetown
- ·
- Mount Standfast
- 0.29 mi to center
10.0Exceptional
(57 Reviews)
1 Bedroom
1 Bath
2 Guests
- Pool
- Ocean View
- Balcony/Terrace
- View
US $201/Night
7 Nights - US $1,407
Villa
10.0Exceptional
(53 Reviews)
4 Bedrooms
3 Baths
8 Guests
3750 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $755/Night
7 Nights - US $5,286
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
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
Apartment
- Holetown
- ·
- Sunset Crest
- 0.04 mi to center
10.0Exceptional
(47 Reviews)
1 Bedroom
1 Bath
2 Guests
750 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $128/Night
7 Nights - US $896
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 $403/Night
7 Nights - US $2,819
Villa
10.0Exceptional
(43 Reviews)
2 Bedrooms
2 Baths
5 Guests
1798 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $332/Night
7 Nights - US $2,322
Villa
- Holetown
- ·
- Mount Standfast
- 0.26 mi to center
10.0Exceptional
(37 Reviews)
4 Bedrooms
4 Baths
8 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $697/Night
7 Nights - US $4,876
Villa
10.0Exceptional
(30 Reviews)
2 Bedrooms
2 Baths
4 Guests
990 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $300/Night
7 Nights - US $2,100
Pet-Friendly Vacation Rentals in Greenwich
Over 74+ Pet-Friendly Vacation Rentals 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 $118/Night
7 Nights - US $823
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
- Oceanfront
- Parking
- Pool
- Ocean View
US $114/Night
7 Nights - US $801
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 $727/Night
7 Nights - US $5,089
House
10.0Exceptional
(2 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $405/Night
7 Nights - US $2,836
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 $922/Night
7 Nights - US $6,452
House
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $361/Night
7 Nights - US $2,530
Apartment
8.0Excellent
(1 Review)
2 Bedrooms
1 Bath
3 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $181/Night
7 Nights - US $1,268
Large Vacation Homes & Villas in Greenwich
Over 1726+ Large Vacation Homes & Villas in or Near Greenwich
Villa
10.0Exceptional
(28 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Pool
Skiing- Ocean View
US $523/Night
7 Nights - US $3,659
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
- 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
House
10.0Exceptional
(20 Reviews)
5 Bedrooms
5 Baths
10 Guests
6500 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $3,567/Night
7 Nights - US $24,968
Villa
- St. Peter
- ·
- Merlin Bay
- 0.60 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
2098.96 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $737/Night
7 Nights - US $5,159
Villa
10.0Exceptional
(18 Reviews)
3 Bedrooms
3 Baths
7 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $258/Night
7 Nights - US $1,804
Villa
- St. James
- ·
- Westmoreland
- 0.50 mi to center
10.0Exceptional
(17 Reviews)
3 Bedrooms
3 Baths
5 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $673/Night
7 Nights - US $4,710
House
- Gibbes
- ·
- Lower Carlton
- 0.27 mi to center
10.0Exceptional
(16 Reviews)
5 Bedrooms
5 Baths
8 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $2,338/Night
7 Nights - US $16,363
Villa
10.0Exceptional
(16 Reviews)
2 Bedrooms
3 Baths
4 Guests
1604 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $408/Night
7 Nights - US $2,854
Wheelchair Accessible Vacation Homes in Greenwich
Over 273+ Wheelchair Accessible Vacation Homes in or Near Greenwich
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 $533/Night
7 Nights - US $3,733
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
Apartment
- Holetown
- ·
- Mount Standfast
- 0.28 mi to center
10.0Exceptional
(9 Reviews)
2 Bedrooms
1 Bath
4 Guests
1100 ft²
- Oceanfront
- Breakfast
- Parking
- Pool
US $377/Night
7 Nights - US $2,641
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
- St. James
- ·
- Old Trees Bay
- 0.26 mi to center
10.0Exceptional
(6 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $539/Night
7 Nights - US $3,770
Apartment
- St. James
- ·
- Old Trees Bay
- 0.23 mi to center
10.0Exceptional
(6 Reviews)
2 Bedrooms
2 Baths
4 Guests
1512 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $418/Night
7 Nights - US $2,928
Apartment
- St. Peter
- ·
- Merlin Bay
- 0.64 mi to center
10.0Exceptional
(6 Reviews)
1 Bedroom
1 Bath
2 Guests
883 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $192/Night
7 Nights - US $1,344
Apartment
10.0Exceptional
(5 Reviews)
2 Bedrooms
2 Baths
5 Guests
1300 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $647/Night
7 Nights - US $4,531
Greenwich Resorts and Airbnb Homes Under $200
Over 272+ Greenwich Resorts and Airbnb Homes Under $200
Cottage
10.0Exceptional
(71 Reviews)
1 Bedroom
1 Bath
2 Guests
750 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $156/Night
7 Nights - US $1,095
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
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 $196/Night
7 Nights - US $1,374
Apartment
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
5 Guests
- Parking
- View
- Air Conditioner
- Internet
US $67/Night
7 Nights - US $469
House
- Holetown
- ·
- Sandy Lane
- 0.21 mi to center
10.0Exceptional
(29 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $176/Night
7 Nights - US $1,231
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 $98/Night
7 Nights - US $686
Cottage
- Holetown
- ·
- Sunset Crest
- 0.04 mi to center
10.0Exceptional
(13 Reviews)
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $142/Night
7 Nights - US $997
Apartment
10.0Exceptional
(9 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $113/Night
7 Nights - US $788
Instantly Bookable Vacation Homes in Greenwich
Over 931+ Instantly Bookable Vacation Homes in or Near Greenwich
House
- Holetown
- ·
- Sunset Crest
- 0.10 mi to center
10.0Exceptional
(26 Reviews)
4 Bedrooms
4 Baths
8 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $412/Night
7 Nights - US $2,887
Apartment
2 Bedrooms
2 Baths
4 Guests
1550 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $434/Night
7 Nights - US $3,035
House
- Holetown
- ·
- Sunset Crest
- 0.12 mi to center
10.0Exceptional
(24 Reviews)
4 Bedrooms
4 Baths
8 Guests
3900 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $771/Night
7 Nights - US $5,399
Condo
- Holetown
- ·
- Mount Standfast
- 0.28 mi to center
10.0Exceptional
(23 Reviews)
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $344/Night
7 Nights - US $2,411
House
10.0Exceptional
(22 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $498/Night
7 Nights - US $3,488
House
- Holetown
- ·
- Sunset Crest
- 0.18 mi to center
10.0Exceptional
(22 Reviews)
3 Bedrooms
2 Baths
6 Guests
1330 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $363/Night
7 Nights - US $2,538
Apartment
- St. James
- ·
- Old Trees Bay
- 0.15 mi to center
10.0Exceptional
(21 Reviews)
1 Bedroom
1 Bath
2 Guests
19375 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $582/Night
7 Nights - US $4,072
House
- Holetown
- ·
- Mount Standfast
- 0.27 mi to center
10.0Exceptional
(18 Reviews)
4 Bedrooms
4 Baths
8 Guests
- Private Pool
- Oceanfront
- Breakfast
- Parking
US $580/Night
7 Nights - US $4,059
Apartment
10.0Exceptional
(17 Reviews)
2 Bedrooms
2 Baths
4 Guests
1193 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $449/Night
7 Nights - US $3,145
Book a Last Minute Place to Stay in Greenwich
About Greenwich Vacation Rentals
Explore over 3178 vacation rentals in Greenwich with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in Greenwich for more space and value.
In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in Greenwich. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Greenwich tailored to your preferences. On average, these rentals offer 1725.06 ft² of space, and are priced at an average of US $1,494 per night.
SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Greenwich at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.
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Top Types of Ski Accommodations in Greenwich
| Type | Count |
|---|---|
| Villas | 1549 |
| Vacation Homes | 780 |
| Holiday Apartments | 620 |
| Cottages | 27 |
| Ski Chalet Rentals | 2 |
| Others | 1 |
Use these Quick Filters to Find a Vacation Rental in Greenwich
★ Pro Tip: Discover Your Ideal Vacation Rental in Greenwich with SunSki Resorts™. Compare a diverse array of properties, including RBO homes, vacation rentals, cottages, cabins, and more. Utilize our advanced filters to search by location, amenities, and price. Book with confidence and enjoy savings of up to 40-60% compared to a hotel stay. Create unforgettable memories with SunSki Resorts™.
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
Sunski 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 in Greenwich?
When organizing your trip to Greenwich, don't miss the chance to explore the top-rated vacation rentals in the vicinity. With a plethora of options available, you're bound to discover the ideal accommodation for your stay in Greenwich. Peruse our collection of highly-rated properties and secure your reservation today.
- Stunning Family Villa with Private Pool Near Beach - Gibbs Glade Villa
- 4 Bed Colonial Style Villa with pool in private setting, short walk to 2 beaches
- *Luxury 4Bed/4Bath Beachfront Villa – Panoramic Ocean Views, Prime Location*
- Idyllic 7 Porters Court, Beach Club Membership, pool, 5min walk beach, Holetown
- Two bed town house with plunge pool in Porters
- Beautiful Family Home with Pool, direct access to tennis courts.
- Delightful garden cottage, realistically priced, near to Gibbs/Mullins beaches
- Superb Penthouse on the exclusive Sugar Hill Resort, with beach membership.
- Stunning West Coast Villa minutes from Mullins Beach
- Designer Penthouse - Amazing Views & Location
How many vacation rentals have private pools in Greenwich?
Uncover 1397 vacation rentals boasting private pools near Greenwich. Explore top-rated RBO homes offering access to a swimming pool:
- Poolside Home, Short Walk to Beach - Turtle View 10
- The Gatehouse
- Royal Westmoreland Benjoli Breeze by Island Villas
- Beach Holiday Rental On Paynes Bay With Stunning Sea Views
Which vacation homes or resorts in Greenwich are best for families?
Choose SunSki for a wide variety of vacation rentals, including family-friendly homes, ski cabins, cottages, and more in Greenwich. Enjoy great views, locations and save money with SunSki Resorts.™
- Sugar Hill, Stunning, 2 Bed 2 Bath Apartment, Pool, Beach Club, Tennis, Golf
- Elegant LUX 2BR 3mins to Beach Pool & Deck
- Kingsgate #1 - by Zenbreak
How many SunSkiResorts vacation rentals or resorts are available in Greenwich?
Discover the ideal vacation rental in Greenwich with SunSki Resorts™. We provide an extensive selection of over 3178 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Greenwich.
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