Gloucester Winter Rental
Apartment
4 Bedrooms
2 Baths
10 Guests
1300 ft²
Oceanfront
Fireplace/Heating
Ocean View
Balcony/Terrace
US $722/Night
7 Nights - US $5,051
House
10.0(1 Review)
5 Bedrooms
2 Baths
10 Guests
2497.23 ft²
Private Beach- Oceanfront
Spa- Fireplace/Heating
US $589/Night
7 Nights - US $4,123
Bed & Breakfast
9.6(322 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
View
US $278/Night
7 Nights - US $1,947
House
3 Bedrooms
3 Baths
6 Guests
24757 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $425/Night
7 Nights - US $2,976
House
10.0(1 Review)
1 Bedroom
2 Baths
7 Guests
- Fireplace/Heating
Parking
Air Conditioner
Internet
US $445/Night
7 Nights - US $3,114
House
10.0(135 Reviews)
2 Bedrooms
1 Bath
5 Guests
1100 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $379/Night
7 Nights - US $2,651
Apartment
9.6(39 Reviews)
1 Bedroom
1 Bath
4 Guests
871.88 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Parking
US $292/Night
7 Nights - US $2,046
House
10.0(72 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $419/Night
7 Nights - US $2,936
Apartment
9.0(64 Reviews)
5 Bedrooms
2 Baths
9 Guests
1087.15 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
Pet Friendly
US $279/Night
7 Nights - US $1,953
House
10.0(49 Reviews)
2 Bedrooms
1 Bath
4 Guests
1150 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $384/Night
7 Nights - US $2,685
House
1 Bedroom
6 Baths
28 Guests
6996.54 ft²
- Oceanfront
Hot Tub- Fireplace/Heating
Pool
US $1,573/Night
7 Nights - US $11,008
House
10.0(35 Reviews)
2 Bedrooms
2 Baths
6 Guests
1376 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $476/Night
7 Nights - US $3,333
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.
Popular Areas for Gloucester Winter Rental
Where are the best neighborhoods to stay in Gloucester?
When planning your stay in Gloucester, Massachusetts, exploring neighborhoods near the waterfront offers a charming and convenient experience for your winter accommodations. These areas provide easy access to local shops and scenic views, making your trip both comfortable and memorable. Staying in a neighborhood close to the historic center allows you to enjoy the authentic atmosphere of Gloucester while benefiting from the tranquility of a cozy retreat.
Annisquam
In this charming area, you'll find a peaceful coastal setting ideal for relaxing winter rentals. This destination offers a serene retreat where you can enjoy the quiet beauty of Massachusetts' coastline during the colder months.
View 333+ Rentals in AnnisquamBest Times to Visit Gloucester
When should you plan your Winter Rental stay?
Identifying the ideal time to visit here can enhance your experience, as seasonal variations influence the atmosphere and availability of winter rentals in this scenic destination known for its charming coastal appeal.
Peak Season Highlights
Summer (June to August)
During the peak summer months, this coastal destination experiences warm weather and longer daylight hours, making it ideal for outdoor activities and enjoying the scenic views.
Average Temperature Daytime: 75-80°F - Nighttime: 60-65°F
Fall (September to November)
Autumn brings vibrant foliage and milder temperatures, providing a picturesque setting that attracts visitors looking for a quiet retreat in the region.
Average Temperature Daytime: 65-70°F - Nighttime: 50-55°F
Off-Season Highlights
Early Spring (March to May)
In the early spring, fewer tourists visit, offering a more peaceful experience with gradually warming weather and blooming landscapes.
Average Temperature Daytime: 50-60°F - Nighttime: 40-45°F
Winter (December to February)
The winter season sees cooler temperatures and occasional snow, creating a charming atmosphere perfect for cozy stays and off-peak exploration in the area.
Average Temperature Daytime: 35-45°F - Nighttime: 25-30°F
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
Outdoor Amenities
- Enjoy outdoor seating areas such as patios or decks to relax and take in the scenic views of the region.
- Take advantage of well-maintained gardens or landscaped yards that enhance your outdoor experience.
- Many properties feature access to private or shared outdoor grilling stations for preparing meals during your stay.
- Look for properties with fire pits or outdoor fireplaces to gather around on chilly evenings.
- Some rentals offer spacious parking areas that accommodate multiple vehicles for easy access to local attractions.
- Experience the convenience of outdoor storage spaces for winter sports gear or recreational equipment.
- If you enjoy water activities, select accommodations with direct access to nearby beaches or waterfronts for scenic strolls and outdoor recreation.
Top Attractions Around Gloucester
What attractions are nearby?
During your stay in this destination, you can explore a variety of outdoor activities such as whale watching excursions, scenic coastal walks, and visiting local art galleries, all conveniently located nearby for a memorable winter experience.
Family Activities
- Sailor's Education Center Discover maritime history and hands-on exhibits that are perfect for engaging young minds during your family visit.
- Bass Rocks Golf Course Enjoy a family-friendly round of golf on this scenic course that offers stunning views and relaxed play suitable for all ages.
- Cripple Cove Conservation Area Explore natural beauty through easy walking trails and scenic overlooks, making it an ideal outdoor activity for families in the area.
- Downtown Gloucester Waterfront Experience the vibrant local culture with waterfront parks, shops, and eateries that provide fun and relaxation for everyone.
Adult Activities
- Whale Watching Tours: Embark on a memorable excursion to observe majestic whales and marine life in their natural habitat just off the coast.
- Visit Gloucester Fishermen’s Memorial: Pay tribute to maritime heritage by exploring this poignant memorial honoring local fishermen, offering both history and scenic views.
- Explore Eastern Point Lighthouse: Take a scenic stroll to this historic lighthouse, renowned for its picturesque setting and captivating ocean vistas.
- Indulge in Fresh Seafood Dining: Savor locally caught seafood at renowned waterfront restaurants, perfect for enjoying authentic regional flavors during your stay.
Other Places to Stay in Gloucester, MA
Dogtown
Good Harbor Beach
Annisquam
Plum Cove Beach
Northeast Hospital Corporation - Addison Gilbert Campus
Cape Ann Museum
Cape Ann Historical Museum
Sargent House Museum
Schooner Adventure
Gloucester Unitarian Universalist Church
Lucky 7 Arcade
Magnolia
Gloucester Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead: Book your winter rental early to secure the best accommodations and location options in this coastal region.
- Explore Local Cuisine: Take advantage of the area's renowned seafood and local eateries to enjoy authentic regional flavors during your stay.
- Dress Appropriately: Prepare for the colder months with layered clothing and waterproof gear to stay comfortable while exploring outdoor activities.
- Discover Hidden Gems: Venture beyond the usual attractions to uncover scenic spots and quiet corners that capture the area's natural beauty.
Transportation Options
- Gloucester Transportation Authority Provides reliable bus services that connect popular areas within the city and to neighboring regions, making local travel convenient for visitors staying in winter rentals here.
- Private Car Rentals Several local agencies offer car rental services, giving you flexible transportation options to explore the scenic coastline and charming neighborhoods at your own pace.
- Taxis and Rideshare Services Taxis and ridesharing apps like Uber and Lyft operate throughout the area, offering quick and easy transportation solutions during your stay in this destination.
- Biking Options Bike rentals and local bike-sharing programs are available for eco-friendly and leisurely explorations of the picturesque waterfront and historic sites nearby.
Local Customs Options
- Sea Shanties: Embracing maritime heritage, locals often sing traditional sea shanties, reflecting the region's historic connection to fishing and seafaring.
- Clam Chowder Culture: Enjoying and sharing hearty clam chowder is a cherished custom, with many eateries serving this regional specialty during winter months.
- Celebration of Lobster: The area has a long-standing tradition of lobster harvesting and festivals that highlight this prized seafood, emphasizing its cultural importance.
- Historic Preservation: Respect for ancient architecture and maritime museums shows the community’s dedication to preserving its rich colonial and fishing history.
Frequently Asked Questions About Gloucester Winter Rentals
1. What are the top Winter Rentals in Gloucester?
There are a lot of options in Gloucester. If you plan on staying in the Gloucester area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Winter Rentals in Gloucester:
- 4 Bedroom LUX House/with Pool Next Door
- WaterViews Overlooking Gloucester Inner Harbor/Sunroom/Deck/Walk to Town/AC
- Walk to Good Harbor Beach. 3BR home, NEW Kitchen
- Stunning Views from Beachfront House in Manchester-by-the-Sea!
- Gloucester Ocean View Escape! Calm, Design-Forward & Minutes to Downtown
- Waterfront Living w Stunning Views, Beautiful Decor, Kayaks, Private drive
- 5-star home with quick walk to 2 beaches!
- Beautiful Oceanfront Home in Estate Setting Gloucester — WINTER RENTAL AVAILABLE
- Evensong: Oceanview Retreat with Dock
- Spacious Modern Beach House- Steps to Long Beach and Good Harbor
2. How many Winter Rentals are available in Gloucester?
Currently, the total number of properties listed by RBO in 2026 is over 167 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.
3. What is the cancellation policy for winter rentals in Gloucester, Massachusetts?
The cancellation policy varies depending on the specific listing you choose. Please review the individual rental's terms and conditions or contact the owner directly for detailed information.
4. Are there any special requirements or restrictions when booking winter accommodations in this area?
Yes, some properties may have specific requirements such as minimum stay durations or age restrictions. You should check the property listing or reach out to the owner for precise details before booking.
5. How do I ensure my winter rental reservation in Gloucester is secure?
Reservations are typically secured through verified listings with provided payment options. For added security, confirm the listing's reviews and contact the owner if needed to verify authenticity before completing your booking.
6. What amenities are generally included in winter rentals around here?
Amenities can vary by property, so it’s best to review each listing carefully. Common features include heating, Wi-Fi, parking, and kitchen facilities. Check the listing details or contact the owner for specific amenities offered.
7. What should I know about the check-in and check-out process for winter accommodations?
Check-in and check-out procedures are outlined in each property listing. Many hosts provide flexible times, but it’s recommended to contact the owner directly beforehand to confirm details and ensure a smooth arrival and departure.
More Rentals You May Like Near Gloucester
House
6 Bedrooms
5 Baths
16 Guests
4919.11 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Parking
US $1,208/Night
7 Nights - US $8,453
House
10.0(32 Reviews)
1 Bedroom
1 Bath
4 Guests
950 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $266/Night
7 Nights - US $1,859
Cottage
10.0(23 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $419/Night
7 Nights - US $2,931
Apartment
10.0(11 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $547/Night
7 Nights - US $3,830
House
10.0(9 Reviews)
2 Bedrooms
3 Baths
7 Guests
1700 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $811/Night
7 Nights - US $5,676
Apartment
10.0(9 Reviews)
1 Bedroom
1 Bath
4 Guests
1000 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $545/Night
7 Nights - US $3,813
Apartment
10.0(5 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $305/Night
7 Nights - US $2,135
Cottage
9.8(105 Reviews)
1 Bedroom
1 Bath
4 Guests
675 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $189/Night
7 Nights - US $1,320
House
9.8(83 Reviews)
1 Bedroom
1 Bath
3 Guests
550 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $256/Night
7 Nights - US $1,791
Apartment
9.8(62 Reviews)
1 Bedroom
1 Bath
3 Guests
500 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $177/Night
7 Nights - US $1,238
Apartment
9.8(60 Reviews)
1 Bedroom
1 Bath
4 Guests
1600 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $541/Night
7 Nights - US $3,784
Cottage
9.8(54 Reviews)
2 Bedrooms
1 Bath
4 Guests
900 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $394/Night
7 Nights - US $2,759
