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Winter Rental Properties
Search Results - 22 Winter Rental Found
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Winter - 10 Fox Run
East Sandwich
Property ID: Zamudio
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Property Info:
4 Bedrooms, Sleeps 6
Style: Cape
3.5 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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Welcome to 10 Fox Run, This charming East Sandwich home features 4 bedrooms, a gourmet kitchen, cozy living room with fireplace, and a terrace level with private patio. Close proximity to highway, beaches and shops. $5000 plus utilities Available Sept. 13, 2025- May 31, 2026.
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Winter - 15 Courtland Drive
Sandwich
Property ID: Marshall
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Property Info:
3 Bedrooms, Sleeps 4
Style: 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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Beautiful 3-bedroom home in Sandwich. Recently renovated in 2023. Located in a quiet, private neighborhood with easy access to beaches and the highway.
$2500 per month, includes WIFI/Cable. Tenant is responsible for heat, electricity, trash removal, and snow removal. WINTER RENTAL: January 12, 2026, through May 1, 2026
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Winter - 173C North Shore Blvd
East Sandwich
Property ID: Thibodeau
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Property Info:
2 Bedrooms, Sleeps 4
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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Completely updated with modern furnishings and amenities, this cottage has central A/C, water views, and is only steps from a private beach. $2150 Per Month, including cable and a mandatory monthly cleaning fee Available November 1, 2025- May 1, 2026
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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, 2025 - May 1st 2026
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Winter - 28 Parsons Lane
East Falmouth
Property ID: Ferris
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Property Info:
5 Bedrooms, Sleeps 5
Style: Contemporary
3 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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Private 5BR, 3BA East Falmouth retreat on 1.63 acres with peekaboo river views, wraparound deck, built-in BBQ, bar, and A/C split units. Pet-friendly with owner approval. Near Waquoit Bay Reserve and Menauhant Beach. $3,200 per month, plus all utilities. The tenant is responsible for trash removal and snow removal. Winter Rental Only Available October 01, 2025, through May 30, 2026 |
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Winter - 2828 Main St
Barnstable
Property ID: Wuellner
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Property Info:
5 Bedrooms, Sleeps 6
Style: Antique
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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Large 5 bedroom, 2.5 Bath antique home on scenic Route 6A in Barnstable. Short term rental. Pets considered with owner approval. Available Jan. 8th, 2026- May 1, 2026 $2,400 per month plus utilities, includes Cable/WIFI
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Winter - 29 Warwick Way
Centerville
Property ID: Ribeiro
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Property Info:
5 Bedrooms, Sleeps 6
Style:
3 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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This spacious 5-bedroom, 3-bathroom winter rental offers cozy comforts with a stone fireplace, fully equipped kitchen, and custom-tiled showers. Enjoy indoor fun with a pool table, fitness equipment, and a kids' play area, plus outdoor activities like a basketball court and playground. Perfect home for your family. Available from October 15th, 2025 to May 1st, 2026 $5000 a month plus utilit
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Winter - 3 Bemis
Sandwich Downs
Property ID: Driscoll
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Property Info:
4 Bedrooms, Sleeps 6
Style: Custom
3 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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Enjoy this beautiful 4-bedroom, 3-bathroom home steps away from a private beach. Available November 05, 2025, until March 31, 2026 $2100 a month, includes WIFI
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Winter - 3 West Rd.
Forestdale
Property ID: Kimball
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Property Info:
2 Bedrooms, Sleeps 4
Style:
1 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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Furnished 2BR Cottage – Cape Cod Comfort At Its Best. Steps to Private Pond. $1950/month, includes WIFI and landscaping. Available August 15, 2025, through May 31, 2026
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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, 2025, through April 30, 2026 $2,600/month, includes WIFI
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Winter - 32 Tupper Avenue
Sandwich
Property ID: AnneseW
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Property Info:
5 Bedrooms, Sleeps 8
Style: colonial
3 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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Gorgeous newer home in Town Neck. Beautiful water views of Cape Cod Bay and the north end of the Cape Cod Canal. Tastefully appointed high end beach home with 3 full baths and 5 bedrooms.
Available November 15, 2025 - April 1, 2026
$5,000 per month plus electric, heat, cable/WIFI, trash removal and snow removal.
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Winter - 36 Wood Ave
Town Neck
Property ID: Paltrineri
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Property Info:
3 Bedrooms, Sleeps 6
Style: Cape
2 Bathrooms
Smoking Not Allowed
Pets Not Allowed
View from Property
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Property Rates:
From $250 p/week night
From $275 p/weekend night
From $1800 p/week
Minimum Stay: 30 Nights
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Spacious 3 bedroom/2 bath home in Town Neck area of Sandwich. $1950 per month - includes internet * Available November 1st, 2025 through May 1st 2026
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Winter - 4 Palmer Rd
Sandwich
Property ID: Kuhn
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Property Info:
4 Bedrooms, Sleeps 2
Style:
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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4-bedroom, 2 1/2 bath colonial located on a cul-de-sac in a quiet neighborhood. Ten-minute drive to the beach and easy access to neighborhood hiking trails and Spectacle Pond
Owner will allow a max occupancy of 2 people small dog ok AVAILABLE OCTOBER 31, 2025 - MAY 15, 2026 $2500.00/MONTH, PLUS ALL UTILITIES
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Winter - 611 Route 6A
East Sandwich
Property ID: Hackett
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Property Info:
5 Bedrooms, Sleeps 9
Style: Cape
2 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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Large updated family-friendly home one mile from private association beach at Carleton Shores East Sandwich. Lovely backyard with a fire pit.
Winter rental available January 3, 2026, through May 1, 2026 $3500 including utilities
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Winter - 69 Knott
Town Neck
Property ID: True
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Property Info:
4 Bedrooms, Sleeps 8
Style: colonial
4 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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The house features a fully equipped open-concept living/kitchen/dining area with quartz counters. The main floor includes a washer and dryer, a master bedroom suite, a second bedroom, and a full bath in the hallway. Upstairs there is another kitchenette/living room, another king suite, a queen bedroom, a hallway bath, and 2nd washer/dryer.Available September 13, 2025, through May 30, 2026
$5000 per month, plus utilities
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Winter - 71 Wing Blvd East
Sandwich Downs
Property ID: Teague
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Property Info:
3 Bedrooms, Sleeps 4
Style: Custom
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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The open floor plan of the living room, dining area, and kitchen creates an inviting space for family and friends. This home features 3 bedrooms and 2 bathrooms Available November 08, 2025, until June 01, 2026 $2100 a month plus utilities
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Winter - 99A North Shore Blvd
East Sandwich
Property ID: Velis99A W
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Property Info:
3 Bedrooms, Sleeps 4
Style: Contemporary
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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Large Contemporary home at East
Sandwich Beach with 3 bedrooms, 2 baths, washer/dryer, dishwasher. Cozy home
where you can spend the winter. Peek-a-boo views of the water and beach
just a few steps away.
Available November 01, 2025 through May 31,
2026.
$2000 per month plus utilities.
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Winter - 99B North Shore Blvd
East Sandwich
Property ID: Velis99BW
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Property Info:
2 Bedrooms, Sleeps 4
Style: Contemporary
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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Waterfront home with unobstructed views of Cape Cod Bay. This 2 bedroom has high ceilings a full bath with tub and shower laundry dishwasher HD flat screen TV and a deck with panoramic views from Plymouth to Provincetown. Kitchen offers a breakfast bar with stools to enjoy the outdoor views as you cook. Spiral staircase leads to an open loft area. SHORT TERM - **WINTER RENTAL* Available Dec. 22nd, 2025- May 23rd 2026
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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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Perfect cottage for those who want to be on the beach for a great price. Two bedrooms one bath and shared pathway to private beach. Available October 15th, 2025 to May 1st, 2026 $1500 per month plus $300 per-month flat fee for utilities.
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Winter - Oceanside 1
East Sandwich
Property ID: Faria
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Property Info:
2 Bedrooms, Sleeps 4
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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This cottage is located directly on desirable East Sandwich Beach. It has 2 bedrooms and two full baths. Available December 05, 2025 - March 31, 2026 $1,900 a month including utilities.
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Winter - Quarterboard 3
East Sandwich
Property ID: GreenW
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Property Info:
2 Bedrooms, Sleeps 3
Style: Cottage
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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SHORT TERM RENTAL - ** WINTER RENTAL** Available November 1, 2025 - May 31, 2026 $1550 per month plus utilities (Includes cable). |
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Winter - Quarterboard 8
East Sandwich
Property ID: GreenW
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Property Info:
2 Bedrooms, Sleeps 3
Style: Cottage
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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SHORT TERM RENTAL - ** WINTER RENTAL** Available November 2, 2025 - May 31, 2026 $1550 per month plus utilities (Includes cable). |
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