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     Winter Rental Properties



     Search Results - 34 Winter Rental Found


1  2  

Winter - 1 Timber Way   
Sandwich
Property ID: Nelligan

Property Info:
2 Bedrooms, Sleeps 4
Style: Ranch
1.5 Bathrooms
Smoking Not Allowed
Pets Allowed


Property Rates:
From $ p/week night
From $ p/weekend night
Minimum Stay: 30 Nights

This cozy home is located in the Lawrence Pond Association with deeded beach rights.

 

Available Sept. 27th 2025 thru May 2nd 2026

 

$1600 per month plus utilities

 



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Winter - 10 Fox Run   
East Sandwich
Property ID: Zamudio

Property Info:
4 Bedrooms, Sleeps 6
Style: Cape
3.5 Bathrooms
Smoking Not Allowed
Pets Allowed


Property Rates:
From $ p/week night
From $ p/weekend night
Minimum Stay: 30 Nights

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 - 110 Knott Ave    
Sandwich
Property ID: Wuerfl

Property Info:
3 Bedrooms, Sleeps 4
Style: 
2 Bathrooms
Smoking Not Allowed
Pets Not Allowed


Property Rates:
From $ p/week night
From $ p/weekend night
Minimum Stay: 30 Nights

Beautiful 3 bedroom home in desired Town Neck of Sandwich. Spend the winter on Cape Cod!

Available October 01, 2025 through May 22, 2026.

$2,500 per month including utilities


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Winter - 111 Popple Bottom Rd   
Sandwich
Property ID: Staples

Property Info:
4 Bedrooms, Sleeps 6
Style: 
3 Bathrooms
Smoking Not Allowed
Pets Allowed
View from Property


Property Rates:
From $ p/week night
From $ p/weekend night
Minimum Stay: 30 Nights

Welcome to 111 Popplebottom Road, a beautifully remodeled home nestled by the serene Lawrence Pond, the largest pond in Sandwich, MA. This home features four bedrooms and three bathrooms, including a master suite with a private bath

 

Available October 1, 2025-May 31, 2026

 

$3200 plus utilities. Includes cable, WIFI and trash pick up.

 



Book Now Send Inquiry View Details





Winter - 115B School St Cotuit   
Cotuit
Property ID: Neshamkin

Property Info:
1 Bedrooms, Sleeps 2
Style: House
1 Bathrooms
Smoking Not Allowed
Pets Allowed


Property Rates:
From $ p/week night
From $ p/weekend night
Minimum Stay: 30 Nights

SHORT TERM RENTAL - **WINTER SEASON** AVAILABLE 09/015/25 to 6/20/26 $1600 A MONTH INCLUDES CABLE, INTERNET, TRASH REMOVAL AND LANDSCAPING. SNOW REMOVAL, ELECTRICITY AND HEAT PUMP ARE THE TENANT'S RESPONSIBILITY. WASHER/DRYER IN BASEMENT WITH BULKHEAD ACCESS.

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Winter - 12 Feake Avenue   
Sandwich
Property ID: Stuber

Property Info:
3 Bedrooms, Sleeps 4
Style: Cape
2 Bathrooms
Smoking Not Allowed
Pets Not Allowed
View from Property


Property Rates:
From $ p/week night
From $ p/weekend night
Minimum Stay: 30 Nights

Beautifully renovated Home at Town Neck Beach in Sandwich with 3 Bedrooms,2 baths with all new furniture.

 

Available October 1st 2025 through June 1st 2026

 

$2400 plus utilties

 



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Winter - 13 Great Hill   
East Sandwich
Property ID: Keegan

Property Info:
3 Bedrooms, Sleeps 6
Style: 
2 Bathrooms
Smoking Not Allowed
Pets Allowed
View from Property
Waterfront Property


Property Rates:
From $ p/week night
From $ p/weekend night
Minimum Stay: 30 Nights

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 15, 2025 - May 1, 2026

 

$2600 PER MONTH PLUS UTILITIES Pets allowed, must be crated if left alone

 



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WInter - 173B North Shore Blvd   
East Sandwich
Property ID: RJR W

Property Info:
2 Bedrooms, Sleeps 2
Style: Cottage
1 Bathrooms
Smoking Not Allowed
Pets Not Allowed
View from Property


Property Rates:
From $ p/week night
From $ p/weekend night
Minimum Stay: 30 Nights

Located in private association with wonderful views of Cape Cod Bay featuring 2 Bedrooms and 1 bathroom.

 

Available December 15, 2025 through May 1, 2026

 

$1,900.00 per month includes all utilities

 



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Winter - 173C North Shore Blvd   
East Sandwich
Property ID: Thibodeau

Property Info:
2 Bedrooms, Sleeps 5
Style: Cottage
1 Bathrooms
Smoking Not Allowed
Pets Not Allowed
View from Property
Waterfront Property


Property Rates:
From $ p/week night
From $ p/weekend night
Minimum Stay: 30 Nights

Completely updated with modern furnishings and amenities this cottage has central A/C, water views, and is only steps to a private beach.

$2150 Per Month including cable and a mandatory monthly cleaning fee



Book Now Send Inquiry View Details





Winter - 18 Great Hill   
Sandwich
Property ID: Spellman

Property Info:
4 Bedrooms, Sleeps 5
Style: Cape
2 Bathrooms
Smoking Not Allowed
Pets Not Allowed
View from Property


Property Rates:
From $ p/week night
From $ p/weekend night
Minimum Stay: 30 Nights

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  
 
                                      


Book Now Send Inquiry View Details





Winter - 203 Phillips   
Sagamore Beach
Property ID: Gefell

Property Info:
2 Bedrooms, Sleeps 2
Style: Cottage
2 Bathrooms
Smoking Not Allowed
Pets Not Allowed
Waterfront Property


Property Rates:
From $ p/week night
From $ p/weekend night
Minimum Stay: 30 Nights

Lovely 1 bedroom cottage at Sagamore Beach. This home offers a bright and clean kitchen, and a cozy living room.

 

Available August 28, 2025 - May 28, 2026

 

$1600 a month plus utilities

 



Book Now Send Inquiry View Details





Winter - 28 Race Lane   
Sandwich
Property ID: Lozano

Property Info:
4 Bedrooms, Sleeps 8
Style: Cape
2.5 Bathrooms
Smoking Not Allowed
Pets Allowed


Property Rates:
From $ p/week night
From $ p/weekend night
Minimum Stay: 30 Nights

Classic Cape style home with a 1 car garage available for Winter Rental in Sandwich! 4 bedrooms and 2.5 bath with washer/dryer and 1 car garage.

Available 09/02/25 through 06/01/26

$3200 including utilties

 



Book Now Send Inquiry View Details





Winter - 2828 Main St    
Barnstable
Property ID: Wuellner

Property Info:
5 Bedrooms, Sleeps 6
Style: Antique
2.5 Bathrooms
Smoking Not Allowed
Pets Allowed


Property Rates:
From $ p/week night
From $ p/weekend night
Minimum Stay: 30 Nights

Large 5 bedroom, 2.5 Bath antique home on scenic Route 6A in Barnstable. Short term rental. Pets considered with owner approval.

Available Sept. 15th, 2025- May 1, 2026

$3,000 per month plus utilities



Book Now Send Inquiry View Details





Winter - 29 Warwick Way   
Centerville
Property ID: Ribeiro

Property Info:
5 Bedrooms, Sleeps 6
Style: 
3 Bathrooms
Smoking Not Allowed
Pets Not Allowed


Property Rates:
From $ p/week night
From $ p/weekend night
Minimum Stay: 30 Nights

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 utilities - gas, electric, cable/wifi. 



Book Now Send Inquiry View Details





Winter - 3 Feake Ave   
Town Neck
Property ID: Hollander

Property Info:
3 Bedrooms, Sleeps 4
Style: Cape
2 Bathrooms
Smoking Not Allowed
Pets Allowed
View from Property


Property Rates:
From $ p/week night
From $ p/weekend night
Minimum Stay: 30 Nights

Cozy home in the Town Neck Beach area. The home has all the amenities you need for a perfect vacation. Just a short distance to the beach and Marina.
$2300 a month. INCLUDES heat, electricity, and trash removal!
Tenant is responsible for cable and wifi


Book Now Send Inquiry View Details





Winter - 32 Tupper Avenue   
Sandwich
Property ID: AnneseW

Property Info:
5 Bedrooms, Sleeps 8
Style: colonial
3 Bathrooms
Smoking Not Allowed
Pets Not Allowed
View from Property


Property Rates:
From $ p/week night
From $ p/weekend night
Minimum Stay: 30 Nights

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.


Book Now Send Inquiry View Details





Winter - 321 Williston Road    
Sagamore Beach
Property ID: Joy

Property Info:
3 Bedrooms, Sleeps 6
Style: Home
2 Bathrooms
Smoking Not Allowed
Pets Allowed


Property Rates:
From $ p/week night
From $ p/weekend night
Minimum Stay: 30 Nights

3 Bedroom 2 Bath home in Sagamore Beach.
No pets. No smoking.

Available for winter rental: 10/01/25-05/31/26



Book Now Send Inquiry View Details





Winter - 36 Wood Ave   
Town Neck
Property ID: Paltrineri

Property Info:
3 Bedrooms, Sleeps 6
Style: Cape
2 Bathrooms
Smoking Not Allowed
Pets Not Allowed
View from Property


Property Rates:
From $250 p/week night
From $275 p/weekend night
From $1800 p/week
Minimum Stay: 30 Nights

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


Book Now Send Inquiry View Details





Winter - 39 Wing Blvd    
Sandwich Downs
Property ID: Ayotte

Property Info:
2 Bedrooms, Sleeps 4
Style: Custom
1 Bathrooms
Smoking Not Allowed
Pets Allowed
View from Property


Property Rates:
From $ p/week night
From $ p/weekend night
Minimum Stay: 30 Nights

Located in the charming Sandwich Downs neighborhood of East Sandwich, MA. This home is tucked away from the main road offering a relaxing setting and a nice walk to a private association beach. Everything you need at a reasonable price! Small dog (under 45 lbs.) allowed with owner approval.

Available 09/13/25-06/01/26   



Book Now Send Inquiry View Details





Winter - 50 Dexter Ave   
Sandwich
Property ID: Coane

Property Info:
2 Bedrooms, Sleeps 4
Style: Custom
1 Bathrooms
Smoking Not Allowed
Pets Not Allowed
View from Property


Property Rates:
From $ p/week night
From $ p/weekend night
Minimum Stay: 30 Nights

This charming home offers a warm living space with beautiful hardwood floors that invites you to unwind after a long day. With two bedrooms, an in-unit laundry, and an additional seating area, this home offers plenty of comfort and convenience.

Available October 02, 2025 until June 1st, 2026

$2600 a month including utilities



Book Now Send Inquiry View Details




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Things to Do in Sandwich

Heritage Museum
Cape Cod & Hyannis Railroad
Green Briar Nature Center and Jam Kitchen
Heritage Museums and Gardens
Sandwich Glass Museum
Sandwich Public Library
Kayak Rentals
MA Fishing License



Things to Do on Cape Cod

Biking on Cape Cod
Cape Cod Baseball League
Cape Cod National Seashore
Hyannis Whale Watching Cruises
The Island Ferry
Deep Sea Fishing
Barnstable County Fair
Cape Cod Scallop Festival
Everything Cape Cod




Local Restaurants

Seafood Sams
Amari Italian and Seafood
Belfry Bistro
Fishermens View
Tomatoes Italian Grill
Pilot House Restaurant
Treehouse Brewery



Useful Links

Availability by week
Pet Friendly Rentals
Linen Rentals by Dune Tootin
Cape Cod Tide Chart
East Sandwich Beach Cottages
Town Neck Beach Rentals
Spring Hill Beach Rentals
Scorton Shores Properties
Sagamore Beach Rentals