Gloucester Winter Rental
Cottage
10.0(279 Reviews)
1 Bedroom
1 Bath
4 Guests
Fireplace/Heating
Ocean View
Balcony/Terrace
View
US $186/Night
7 Nights - US $1,305
RV Rental
8.6(25 Reviews)
1 Bedroom
1 Bath
Oceanfront
Hot Tub- Fireplace/Heating
Pool
US $157/Night
7 Nights - US $1,099
Cottage
10.0(186 Reviews)
2 Bedrooms
2 Baths
4 Guests
1500 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
Kitchen
US $288/Night
7 Nights - US $2,013
House
10.0(112 Reviews)
2 Bedrooms
1 Bath
4 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly- Kitchen
US $143/Night
7 Nights - US $1,002
House
10.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
940 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
Parking
US $185/Night
7 Nights - US $1,292
Cottage
9.8(31 Reviews)
2 Bedrooms
1 Bath
4 Guests
1100 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $143/Night
7 Nights - US $999
Apartment
9.8(6 Reviews)
2 Bedrooms
1 Bath
7 Guests
900 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $252/Night
7 Nights - US $1,767
House
9.4(32 Reviews)
2 Bedrooms
1 Bath
6 Guests
1200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $233/Night
7 Nights - US $1,629
House
10.0(58 Reviews)
3 Bedrooms
2 Baths
6 Guests
1800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $217/Night
7 Nights - US $1,519
House
10.0(25 Reviews)
3 Bedrooms
3 Baths
10 Guests
2200 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- View
US $421/Night
7 Nights - US $2,946
House
9.8(157 Reviews)
3 Bedrooms
2 Baths
6 Guests
1450 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $338/Night
7 Nights - US $2,365
House
9.4(26 Reviews)
4 Bedrooms
2 Baths
10 Guests
2400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $504/Night
7 Nights - US $3,525
Why Choose Rent By Owner for your Gloucester Winter Rental?
What makes our Winter Rental special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Gloucester
How to Book Your Gloucester Winter Rental
What's our booking process?
Our platform allows you to browse a curated selection of winter rental. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Gloucester
Common Winter Rental Amenities
What amenities can you expect?
Our Winter Rental are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in Gloucester, VA
Rosewell Ruins
Schley
Ware Neck
Zanoni
Gloucester Museum of History
Riverside Walter Reed Hospital
Petsworth
Gloucester County
Gloucester Winter Rental Frequently Asked Questions
1. How many Winter Rentals are available in Gloucester?
Currently, the total number of properties listed by RBO in 2026 is over 24 in the Gloucester area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Winter Rentals in Gloucester.
More Rentals You May Like Near Gloucester
House
9.2(10 Reviews)
4 Bedrooms
3 Baths
8 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $733/Night
7 Nights - US $5,133
House
7.8(19 Reviews)
3 Bedrooms
2 Baths
7 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $232/Night
7 Nights - US $1,621
House
9.2(10 Reviews)
9 Bedrooms
7 Baths
22 Guests
3800 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,271/Night
7 Nights - US $8,897
House
10.0(72 Reviews)
2 Bedrooms
1 Bath
6 Guests
Private Pool- Fireplace/Heating
- Pool
- Ocean View
US $403/Night
7 Nights - US $2,821
House
10.0(21 Reviews)
3 Bedrooms
1 Bath
10 Guests
1450 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $202/Night
7 Nights - US $1,415
House
10.0(6 Reviews)
3 Bedrooms
3 Baths
10 Guests
2549 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $418/Night
7 Nights - US $2,925
Other
10.0(71 Reviews)
3 Bedrooms
2 Baths
8 Guests
2300 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $333/Night
7 Nights - US $2,330
House
10.0(16 Reviews)
6 Bedrooms
4 Baths
10 Guests
3200 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Kitchen
US $719/Night
7 Nights - US $5,032
House
9.8(10 Reviews)
3 Bedrooms
2 Baths
8 Guests
1100 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $219/Night
7 Nights - US $1,535
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
Spa- Fireplace/Heating
- Pool
- Ocean View
US $178/Night
7 Nights - US $1,247
Cottage
9.8(23 Reviews)
2 Bedrooms
1 Bath
4 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $268/Night
7 Nights - US $1,874
Other
9.8(120 Reviews)
3 Bedrooms
2 Baths
10 Guests
1500 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $262/Night
7 Nights - US $1,833
