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Winter Rental Properties
Search Results - 17 Winter Rental Found
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Winter - 111 Popple Bottom Rd
Sandwich
Property ID: Staples
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Property Info:
4 Bedrooms, Sleeps 6
Style:
3 Bathrooms
Smoking Not Allowed
Pets Allowed
View from Property
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Property Rates:
From $ p/week night
From $ p/weekend night
Minimum Stay: 30 Nights
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Welcome to 111 Popplebottom Road, a beautifully remodeled waterfront home overlooking Lawrence Pond, the largest pond in Sandwich, MA. Featuring four bedrooms and three bathrooms, including a private primary suite, this home combines comfort with scenic charm. Each bedroom enjoys tranquil water views, making it easy to unwind and fully embrace pondside living. Available October 1, 2026-May 31, 2027 $3,200/ month. Owner will provide weekly trash/recycling pick up, cable, and WIFI. Tenant is responsible for oil heat, electric/gas, and any needed snow removal
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Winter - 113 North Shore Blvd. Unit 3
East Sandwich
Property ID: Winter - 113NSB#3
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Property Info:
2 Bedrooms, Sleeps 3
Style: Cottage
2 Bathrooms
Smoking Not Allowed
Pets Not Allowed
View from Property
Waterfront Property
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Property Rates:
From $ p/week night
From $ p/weekend night
Minimum Stay: 30 Nights
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Newly remodeled 2 bedroom 2 bath unit in a four-unit beachfront property with great views of the marsh and partial views of Cape Cod Bay. Fully furnished with washer and dryer.
$2,000.00 per month includes ALL utilties & internet. Available October 3, 2026 through May 01, 2027
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Winter - 12 Feake Avenue
Sandwich
Property ID: Stuber
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Property Info:
3 Bedrooms, Sleeps 4
Style: Cape
2 Bathrooms
Smoking Not Allowed
Pets Allowed
View from Property
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Property Rates:
From $ p/week night
From $ p/weekend night
Minimum Stay: 30 Nights
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Gorgeous Town Neck home with open-concept living, modern kitchen, fireplace, and 3 spacious bedrooms Available October 1st, 2026 through May 22, 2027 $2300 plus utilities
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Winter - 13 Great Hill
East Sandwich
Property ID: Keegan
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Property Info:
3 Bedrooms, Sleeps 6
Style:
2 Bathrooms
Smoking Not Allowed
Pets Allowed
View from Property
Waterfront Property
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Property Rates:
From $ p/week night
From $ p/weekend night
Minimum Stay: 30 Nights
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An acre and a half of pure beauty on a lake where no motorboats are allowed. Private beach and your own floating dock and firepit lakeside. The home is elegantly renovated with beautiful design details and state-of-the-art amenities. Available September 1, 2026 - May 1, 2027 $2750 PER MONTH PLUS UTILITIES Pets allowed, must be crated if left alone
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Winter - 18 Great Hill
Sandwich
Property ID: Spellman
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Property Info:
4 Bedrooms, Sleeps 5
Style: Cape
2 Bathrooms
Smoking Not Allowed
Pets Not Allowed
View from Property
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Property Rates:
From $ p/week night
From $ p/weekend night
Minimum Stay: 30 Nights
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Family friendly cape right across the street from Lawrence pond beach and tennis courts$6000 a month plus utilities September 15th, 2026 - May 1st 2027 |
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Winter - 3 Fern Avenue
East Sandwich
Property ID: Loughlin
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Property Info:
2 Bedrooms, Sleeps 4
Style: Ranch
1 Bathrooms
Smoking Not Allowed
Pets Not Allowed
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Property Rates:
From $ p/week night
From $ p/weekend night
Minimum Stay: 30 Nights
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Lovely private side street in East Sandwich is where you will find this remodeled 2-bedroom, 1-bath home with washer and dryer $1800 per month plus utilities - includes Wi-fi and trash removal in the monthly rent. Available October 15, 2026 - April 30, 2027
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Winter - 32 Madison Drive
East Sandwich
Property ID: Reardon
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Property Info:
2 Bedrooms, Sleeps 4
Style:
2 Bathrooms
Smoking Not Allowed
Pets Not Allowed
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Property Rates:
From $ p/week night
From $ p/weekend night
Minimum Stay: 30 Nights
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Relax in this comfortable East Sandwich retreat, featuring 2 bedrooms, 2 baths, a sunny deck with a gas grill, and a fire pit for evenings under the stars. Winter Rental Only Available October 1, 2026, through April 30, 2027 $2,600/month, includes WIFI
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Winter - 505 Main St.
Barnstable
Property ID: Morillo
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Property Info:
4 Bedrooms, Sleeps 4
Style:
2.5 Bathrooms
Smoking Not Allowed
Pets Not Allowed
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Property Rates:
From $ p/week night
From $ p/weekend night
Minimum Stay: 30 Nights
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Welcome to your luxury Cape Cod retreat in West Barnstable! This 4-bedroom, 2.5-bath home has been completely rennovated and is awaiting you and your family for a winter stay.
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Winter - 56 Wood Avenue
Sandwich
Property ID: 56Wood-Winter
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Property Info:
2 Bedrooms, Sleeps 4
Style: Cottage
1.5 Bathrooms
Smoking Not Allowed
Pets Allowed
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Property Rates:
From $ p/week night
From $ p/weekend night
Minimum Stay: 30 Nights
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Clean and bright kitchen and wood floors. 2 Bedrooms, 1.5 bathrooms, nice living area. Lovely deck with a peaceful backyard. $1,950 per month plus utilities Available Sept. 1, 2026 - May 31, 2027
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Winter - 6 Beachway Road
East Sandwich
Property ID: Fisher
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Property Info:
3 Bedrooms, Sleeps 5
Style: Brick ranch
1.5 Bathrooms
Smoking Not Allowed
Pets Allowed
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Property Rates:
From $ p/week night
From $ p/weekend night
Minimum Stay: 30 Nights
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3 Bedroom, 1.5 bath home at Sandwich Downs available for winter rental. $2200 per month plus utilities. Available Sept. 15th 2026- May 15th, 2027
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Winter - 68 Town Neck Rd
Sandwich
Property ID: Reader-W
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Property Info:
4 Bedrooms, Sleeps 2
Style: Cape
2.5 Bathrooms
Smoking Not Allowed
Pets Allowed
View from Property
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Property Rates:
From $ p/week night
From $ p/weekend night
Minimum Stay: 30 Nights
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Located in Town Neck and 0.2 miles to the public beach and local waterfront restaurant is this beautiful home with 4 bedrooms and 2.5 bathrooms. **Small pet allowed with owner approval. $2000 per month plus utilities - basic cable and Wi-Fi included in monthly rent Available Oct. 1st, 2026- May 31st, 2027
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Winter - 72 Bay Rd
North Falmouth
Property ID: Kofman
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Property Info:
3 Bedrooms, Sleeps 6
Style: Colonial
2.5 Bathrooms
Smoking Not Allowed
Pets Allowed
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Property Rates:
From $ p/week night
From $ p/weekend night
Minimum Stay: 30 Nights
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Updated 3 bedroom colonial minutes to Megansett Beach in North Falmouth! Bring a small dog with prior approval.
Available October 1st, 2026 to April 30, 2027 $2800 per month plus utilities
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Winter - 79 B North Shore Blvd
East Sandwich
Property ID: Dean
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Property Info:
1 Bedrooms, Sleeps 2
Style: Cottage by the beach
1 Bathrooms
Smoking Not Allowed
Pets Allowed
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Property Rates:
From $ p/week night
From $ p/weekend night
Minimum Stay: 30 Nights
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Guest cottage at Oceanfront property. Comfortable one-bedroom cottage with new windows and a recent bathroom update. Relax and enjoy the ocean breezes. Small dog allowed. $1,300 a month. Includes trash removal, water, and sewage. Winter rental 10/5/2026 through 5/03/2027
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Winter - 96 Knott Ave
Town Neck
Property ID: 96 Knott Ave LLC
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Property Info:
2 Bedrooms, Sleeps 2
Style: contemporary
2 Bathrooms
Smoking Not Allowed
Pets Not Allowed
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Property Rates:
From $ p/week night
From $ p/weekend night
Minimum Stay: 30 Nights
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A charming and cozy Cape Cod style home located in the heart of Town Neck. $2600 a month plus utilities. Available Oct. 1st, 2026- May 1st, 2027
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Winter - Dune Tootin bungalow
East Sandwich
Property ID: 113NSBBungalow
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Property Info:
1 Bedrooms, Sleeps 1
Style: Cottage at the beach
1 Bathrooms
Smoking Not Allowed
Pets Not Allowed
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Property Rates:
From $ p/week night
From $ p/weekend night
Minimum Stay: 30 Nights
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Clean and cozy lower-level studio unit in a Beachfront property. Kitchen, living area and 1 bedroom. Bedroom #1--Double 1 Person only, washer and dryer
Available September 05, 2026 to May 05, 2027 $1400 a month, includes ALL utilities
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Winter - Dune Tootin Unit 1
East Sandwich
Property ID: 113NSB#1
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Property Info:
2 Bedrooms, Sleeps 2
Style: Cottage
1 Bathrooms
Smoking Not Allowed
Pets Not Allowed
View from Property
Waterfront Property
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Property Rates:
From $ p/week night
From $ p/weekend night
Minimum Stay: 30 Nights
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Adorable waterfront unit in a three-unit property located right on East Sandwich beach. 2 Bedrooms, bath with shower, laundry and internet. Enjoy the serene views of Cape Cod Bay. 2 parking spaces and trash pick-up included. Private pathway to the beach.Available September 25, 2026 to May 1, 2027 $2200 includes all utilities. |
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Winter - Dune Tootin Unit 2
East Sandwich
Property ID: 113NSB#2
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Property Info:
2 Bedrooms, Sleeps 2
Style: Cottage
1 Bathrooms
Smoking Not Allowed
Pets Not Allowed
View from Property
Waterfront Property
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Property Rates:
From $ p/week night
From $ p/weekend night
Minimum Stay: 30 Nights
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Clean and cozy two-bedroom unit in a three-unit beachfront property, offering beautiful views of Cape Cod Bay and a great sandbar at low tide. Make this your cozy winter retreat on the beach! $1800, includes ALL utilties. Available September 20, 2026 through May 1, 2027
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