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Holiday Homes near Cape Cod Rail Trail

Brewster, Massachusetts 02631
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Bedrooms

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5 km
301 rentals in Brewster.
New Listing at Ocean Edge- Guest Passes Available, holiday rental in Brewster
New Listing at Ocean Edge- Guest Passes Available, holiday rental in Brewster
New Listing at Ocean Edge- Guest Passes Available, holiday rental in Brewster

New Listing at Ocean Edge- Guest Passes Available

Condo/Apartment
1.9 kilometres from Cape Cod Rail Trail
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail, holiday rental in Brewster
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail, holiday rental in Brewster
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail, holiday rental in Brewster

Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

Holiday Rental House
2.1 kilometres from Cape Cod Rail Trail
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Charming Beach Cottage - Walk To Beach, holiday rental in Brewster
Charming Beach Cottage - Walk To Beach, holiday rental in Brewster
Charming Beach Cottage - Walk To Beach, holiday rental in Brewster

Charming Beach Cottage - Walk To Beach

Holiday Rental House
3.4 kilometres from Cape Cod Rail Trail
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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!SEPT SALE!-Private Heated Pool! Renovated 5BD3BA,AC, Near Beaches and Nickerson, holiday rental in Brewster
!SEPT SALE!-Private Heated Pool! Renovated 5BD3BA,AC, Near Beaches and Nickerson, holiday rental in Brewster
!SEPT SALE!-Private Heated Pool! Renovated 5BD3BA,AC, Near Beaches and Nickerson, holiday rental in Brewster

!SEPT SALE!-Private Heated Pool! Renovated 5BD3BA,AC, Near Beaches and Nickerson

Holiday Rental House
2.6 kilometres from Cape Cod Rail Trail
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Charming second-floor retreat with a full kitchen and balcony view, holiday rental in Brewster
Charming second-floor retreat with a full kitchen and balcony view, holiday rental in Brewster
Charming second-floor retreat with a full kitchen and balcony view, holiday rental in Brewster

Charming second-floor retreat with a full kitchen and balcony view

Condo/Apartment
1.9 kilometres from Cape Cod Rail Trail
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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A SHORT STROLL TO LINNELL LANDING BEACH - BOOK NOW FOR SUMMER 2025!, holiday rental in Brewster
A SHORT STROLL TO LINNELL LANDING BEACH - BOOK NOW FOR SUMMER 2025!, holiday rental in Brewster
A SHORT STROLL TO LINNELL LANDING BEACH - BOOK NOW FOR SUMMER 2025!, holiday rental in Brewster

A SHORT STROLL TO LINNELL LANDING BEACH - BOOK NOW FOR SUMMER 2025!

Holiday Rental House
4.0 kilometres from Cape Cod Rail Trail
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Newly Remodel.  Ocean Edge Resort.  A/C all rooms. 1 King, 1 Queen & 2 Twin, holiday rental in Brewster
Newly Remodel.  Ocean Edge Resort.  A/C all rooms. 1 King, 1 Queen & 2 Twin, holiday rental in Brewster
Newly Remodel.  Ocean Edge Resort.  A/C all rooms. 1 King, 1 Queen & 2 Twin, holiday rental in Brewster

Newly Remodel. Ocean Edge Resort. A/C all rooms. 1 King, 1 Queen & 2 Twin

Holiday Rental House
2.6 kilometres from Cape Cod Rail Trail
3 bedrooms
2 bathrooms
Sleeps 6
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Less Than 1 Mile to Beach with Custom Fire Pit!, holiday rental in Brewster
Less Than 1 Mile to Beach with Custom Fire Pit!, holiday rental in Brewster
Less Than 1 Mile to Beach with Custom Fire Pit!, holiday rental in Brewster

Less Than 1 Mile to Beach with Custom Fire Pit!

Holiday Rental House
2.3 kilometres from Cape Cod Rail Trail
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Pond Front Home with Private Dock!, holiday rental in Brewster
Pond Front Home with Private Dock!, holiday rental in Brewster
Pond Front Home with Private Dock!, holiday rental in Brewster

Pond Front Home with Private Dock!

Holiday Rental House
1.4 kilometres from Cape Cod Rail Trail
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Great Couples Summer Getaway, holiday rental in Brewster
Great Couples Summer Getaway, holiday rental in Brewster
Great Couples Summer Getaway, holiday rental in Brewster

Great Couples Summer Getaway

Condo/Apartment
1.4 kilometres from Cape Cod Rail Trail
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Bayside Apt, holiday rental in Brewster
Bayside Apt, holiday rental in Brewster
Bayside Apt, holiday rental in Brewster

Bayside Apt

Condo/Apartment
1.4 kilometres from Cape Cod Rail Trail
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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The Condo at Ocean Edge, holiday rental in Brewster
The Condo at Ocean Edge, holiday rental in Brewster
The Condo at Ocean Edge, holiday rental in Brewster

The Condo at Ocean Edge

Condo/Apartment
2.1 kilometres from Cape Cod Rail Trail
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Secluded Hideaway Sleeps 4 Monthly $5000., holiday rental in Brewster
Secluded Hideaway Sleeps 4 Monthly $5000., holiday rental in Brewster
Secluded Hideaway Sleeps 4 Monthly $5000., holiday rental in Brewster

Secluded Hideaway Sleeps 4 Monthly $5000.

Condo/Apartment
1.4 kilometres from Cape Cod Rail Trail
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Charming Cape Cottage in Brewster, holiday rental in Brewster
Charming Cape Cottage in Brewster, holiday rental in Brewster
Charming Cape Cottage in Brewster, holiday rental in Brewster

Charming Cape Cottage in Brewster

Holiday Rental House
2.3 kilometres from Cape Cod Rail Trail
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Newly renovated 2 bedroom cottage - walk to beach, holiday rental in Brewster
Newly renovated 2 bedroom cottage - walk to beach, holiday rental in Brewster
Newly renovated 2 bedroom cottage - walk to beach, holiday rental in Brewster

Newly renovated 2 bedroom cottage - walk to beach

Holiday Rental House
4.2 kilometres from Cape Cod Rail Trail
2 bedrooms
1 bathroom
Sleeps 5
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Winter Retreat! Cottage- like Cape Cod Home, wooded, quiet and serene., holiday rental in Brewster
Winter Retreat! Cottage- like Cape Cod Home, wooded, quiet and serene., holiday rental in Brewster
Winter Retreat! Cottage- like Cape Cod Home, wooded, quiet and serene., holiday rental in Brewster

Winter Retreat! Cottage- like Cape Cod Home, wooded, quiet and serene.

Holiday Rental House
1.6 kilometres from Cape Cod Rail Trail
2 bedrooms
2 bathrooms
Sleeps 5
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Charming Condo in the heart of Ocean Edge Resort, holiday rental in Brewster
Charming Condo in the heart of Ocean Edge Resort, holiday rental in Brewster
Charming Condo in the heart of Ocean Edge Resort, holiday rental in Brewster

Charming Condo in the heart of Ocean Edge Resort

Condo/Apartment
2.3 kilometres from Cape Cod Rail Trail
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Cape Cod Resort Condo, holiday rental in Brewster
Cape Cod Resort Condo, holiday rental in Brewster
Cape Cod Resort Condo, holiday rental in Brewster

Cape Cod Resort Condo

Condo/Apartment
2.3 kilometres from Cape Cod Rail Trail
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Private Beach.  Fabulous Bay Views. WIFI, holiday rental in Brewster
Private Beach.  Fabulous Bay Views. WIFI, holiday rental in Brewster
Private Beach.  Fabulous Bay Views. WIFI, holiday rental in Brewster

Private Beach. Fabulous Bay Views. WIFI

Holiday Rental House
2.9 kilometres from Cape Cod Rail Trail
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Newly Renovated Coveted Sheep Pond Estates/Walk to Pond,Families love it, holiday rental in Brewster
Newly Renovated Coveted Sheep Pond Estates/Walk to Pond,Families love it, holiday rental in Brewster
Newly Renovated Coveted Sheep Pond Estates/Walk to Pond,Families love it, holiday rental in Brewster

Newly Renovated Coveted Sheep Pond Estates/Walk to Pond,Families love it

Holiday Rental House
1.3 kilometres from Cape Cod Rail Trail
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Authentic Cape Cod Saltbox - Antique home with modern conveniences, holiday rental in Brewster
Authentic Cape Cod Saltbox - Antique home with modern conveniences, holiday rental in Brewster
Authentic Cape Cod Saltbox - Antique home with modern conveniences, holiday rental in Brewster

Authentic Cape Cod Saltbox - Antique home with modern conveniences

Holiday Rental House
4.0 kilometres from Cape Cod Rail Trail
2 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
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Billington townhouse with straight staircase that leads to an enclosed loft, holiday rental in Brewster
Billington townhouse with straight staircase that leads to an enclosed loft, holiday rental in Brewster
Billington townhouse with straight staircase that leads to an enclosed loft, holiday rental in Brewster

Billington townhouse with straight staircase that leads to an enclosed loft

Condo/Apartment
1.3 kilometres from Cape Cod Rail Trail
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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This B-Style Billington Village townhouse has access to Golf and Pool. (Fees, holiday rental in Brewster
This B-Style Billington Village townhouse has access to Golf and Pool. (Fees, holiday rental in Brewster
This B-Style Billington Village townhouse has access to Golf and Pool. (Fees, holiday rental in Brewster

This B-Style Billington Village townhouse has access to Golf and Pool. (Fees

Condo/Apartment
0.6 kilometres from Cape Cod Rail Trail
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Pets Considered Brewster rental!, holiday rental in Brewster
Pets Considered Brewster rental!, holiday rental in Brewster
Pets Considered Brewster rental!, holiday rental in Brewster

Pets Considered Brewster rental!

Holiday Rental House
2.6 kilometres from Cape Cod Rail Trail
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Wonderful freestanding condo in Ocean Edge in Allerton Village., holiday rental in Brewster
Wonderful freestanding condo in Ocean Edge in Allerton Village., holiday rental in Brewster
Wonderful freestanding condo in Ocean Edge in Allerton Village., holiday rental in Brewster

Wonderful freestanding condo in Ocean Edge in Allerton Village.

Condo/Apartment
1.8 kilometres from Cape Cod Rail Trail
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Only a Half of a mile to Crosby Landing Beach in Brewster on Cape Cod Bay. Pets, holiday rental in Brewster
Only a Half of a mile to Crosby Landing Beach in Brewster on Cape Cod Bay. Pets, holiday rental in Brewster
Only a Half of a mile to Crosby Landing Beach in Brewster on Cape Cod Bay. Pets, holiday rental in Brewster

Only a Half of a mile to Crosby Landing Beach in Brewster on Cape Cod Bay. Pets

Holiday Rental House
4.7 kilometres from Cape Cod Rail Trail
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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3-Bedroom Oceanfront Cottage with Private Beach, holiday rental in Brewster
3-Bedroom Oceanfront Cottage with Private Beach, holiday rental in Brewster
3-Bedroom Oceanfront Cottage with Private Beach, holiday rental in Brewster

3-Bedroom Oceanfront Cottage with Private Beach

Holiday Rental House
3.2 kilometres from Cape Cod Rail Trail
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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FABULOUS CAPE COD RESORT !, holiday rental in Brewster
FABULOUS CAPE COD RESORT !, holiday rental in Brewster
FABULOUS CAPE COD RESORT !, holiday rental in Brewster

FABULOUS CAPE COD RESORT !

Holiday Rental House
2.4 kilometres from Cape Cod Rail Trail
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Completely remodeled end unit!, holiday rental in Brewster
Completely remodeled end unit!, holiday rental in Brewster
Completely remodeled end unit!, holiday rental in Brewster

Completely remodeled end unit!

Condo/Apartment
1.9 kilometres from Cape Cod Rail Trail
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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A lovely, warm and inviting property to spend some quality and relaxing time., holiday rental in Brewster
A lovely, warm and inviting property to spend some quality and relaxing time., holiday rental in Brewster
A lovely, warm and inviting property to spend some quality and relaxing time., holiday rental in Brewster

A lovely, warm and inviting property to spend some quality and relaxing time.

Holiday Rental House
0.8 kilometres from Cape Cod Rail Trail
2 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
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Immaculately Clean - Continually  Updated – Ocean Edge, holiday rental in Brewster
Immaculately Clean - Continually  Updated – Ocean Edge, holiday rental in Brewster
Immaculately Clean - Continually  Updated – Ocean Edge, holiday rental in Brewster

Immaculately Clean - Continually Updated – Ocean Edge

Condo/Apartment
1.9 kilometres from Cape Cod Rail Trail
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Little slice of Heaven in Ocean Edge near Lynx Tavern and Arbor pool!, holiday rental in Brewster
Little slice of Heaven in Ocean Edge near Lynx Tavern and Arbor pool!, holiday rental in Brewster
Little slice of Heaven in Ocean Edge near Lynx Tavern and Arbor pool!, holiday rental in Brewster

Little slice of Heaven in Ocean Edge near Lynx Tavern and Arbor pool!

Condo/Apartment
1.4 kilometres from Cape Cod Rail Trail
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Beautiful Brewster Green Resort Condo with Many Amenities, holiday rental in Brewster
Beautiful Brewster Green Resort Condo with Many Amenities, holiday rental in Brewster
Beautiful Brewster Green Resort Condo with Many Amenities, holiday rental in Brewster

Beautiful Brewster Green Resort Condo with Many Amenities

Condo/Apartment
2.3 kilometres from Cape Cod Rail Trail
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Completely remodeled Billington townhouse with delightful decor offering two, holiday rental in Brewster
Completely remodeled Billington townhouse with delightful decor offering two, holiday rental in Brewster
Completely remodeled Billington townhouse with delightful decor offering two, holiday rental in Brewster

Completely remodeled Billington townhouse with delightful decor offering two

Condo/Apartment
1.3 kilometres from Cape Cod Rail Trail
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Walk to Beach Dog Welcome!, holiday rental in Brewster
Walk to Beach Dog Welcome!, holiday rental in Brewster
Walk to Beach Dog Welcome!, holiday rental in Brewster

Walk to Beach Dog Welcome!

Holiday Rental House
2.6 kilometres from Cape Cod Rail Trail
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Spacious upper-level luxurious Endicott unit with golf access, just steps to, holiday rental in Brewster
Spacious upper-level luxurious Endicott unit with golf access, just steps to, holiday rental in Brewster
Spacious upper-level luxurious Endicott unit with golf access, just steps to, holiday rental in Brewster

Spacious upper-level luxurious Endicott unit with golf access, just steps to

Condo/Apartment
1.4 kilometres from Cape Cod Rail Trail
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Approximately one mile away from the bike trail and Nickerson State Park, holiday rental in Brewster
Approximately one mile away from the bike trail and Nickerson State Park, holiday rental in Brewster
Approximately one mile away from the bike trail and Nickerson State Park, holiday rental in Brewster

Approximately one mile away from the bike trail and Nickerson State Park

Holiday Rental House
2.6 kilometres from Cape Cod Rail Trail
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Classy, Comfy, and Convenient with AC & Pool Access, holiday rental in Brewster
Classy, Comfy, and Convenient with AC & Pool Access, holiday rental in Brewster
Classy, Comfy, and Convenient with AC & Pool Access, holiday rental in Brewster

Classy, Comfy, and Convenient with AC & Pool Access

Condo/Apartment
1.9 kilometres from Cape Cod Rail Trail
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful Brewster Condo in Ocean Edge, Nearby Beaches, Cape Rail Trail, holiday rental in Brewster
Beautiful Brewster Condo in Ocean Edge, Nearby Beaches, Cape Rail Trail, holiday rental in Brewster
Beautiful Brewster Condo in Ocean Edge, Nearby Beaches, Cape Rail Trail, holiday rental in Brewster

Beautiful Brewster Condo in Ocean Edge, Nearby Beaches, Cape Rail Trail

Condo/Apartment
2.1 kilometres from Cape Cod Rail Trail
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Inviting private patio, charming décor, and a wonderful location close to Pool, holiday rental in Brewster
Inviting private patio, charming décor, and a wonderful location close to Pool, holiday rental in Brewster
Inviting private patio, charming décor, and a wonderful location close to Pool, holiday rental in Brewster

Inviting private patio, charming décor, and a wonderful location close to Pool

Condo/Apartment
2.4 kilometres from Cape Cod Rail Trail
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming Patio, Quiet, Clean, Pool & Fitness Access (Fee Paid to Ocean Edge), holiday rental in Brewster
Charming Patio, Quiet, Clean, Pool & Fitness Access (Fee Paid to Ocean Edge), holiday rental in Brewster
Charming Patio, Quiet, Clean, Pool & Fitness Access (Fee Paid to Ocean Edge), holiday rental in Brewster

Charming Patio, Quiet, Clean, Pool & Fitness Access (Fee Paid to Ocean Edge)

Holiday Rental House
1.3 kilometres from Cape Cod Rail Trail
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Brewster Village Retreat! With 3 BR, 2 Bath, 4 ACs, Sleep Sofa (Sleeps 6) close, holiday rental in Brewster
Brewster Village Retreat! With 3 BR, 2 Bath, 4 ACs, Sleep Sofa (Sleeps 6) close, holiday rental in Brewster
Brewster Village Retreat! With 3 BR, 2 Bath, 4 ACs, Sleep Sofa (Sleeps 6) close, holiday rental in Brewster

Brewster Village Retreat! With 3 BR, 2 Bath, 4 ACs, Sleep Sofa (Sleeps 6) close

Holiday Rental House
1.3 kilometres from Cape Cod Rail Trail
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Relax and enjoy the fine residence in beautiful Sea Pines on Cape Cod Bay!, holiday rental in Brewster
Relax and enjoy the fine residence in beautiful Sea Pines on Cape Cod Bay!, holiday rental in Brewster
Relax and enjoy the fine residence in beautiful Sea Pines on Cape Cod Bay!, holiday rental in Brewster

Relax and enjoy the fine residence in beautiful Sea Pines on Cape Cod Bay!

Condo/Apartment
2.7 kilometres from Cape Cod Rail Trail
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Absolutely beautiful and updated Ocean Edge Condo in Brewster!, holiday rental in Brewster
Absolutely beautiful and updated Ocean Edge Condo in Brewster!, holiday rental in Brewster
Absolutely beautiful and updated Ocean Edge Condo in Brewster!, holiday rental in Brewster

Absolutely beautiful and updated Ocean Edge Condo in Brewster!

Condo/Apartment
2.1 kilometres from Cape Cod Rail Trail
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Centrally Located Private Corner Unit, holiday rental in Brewster
Centrally Located Private Corner Unit, holiday rental in Brewster
Centrally Located Private Corner Unit, holiday rental in Brewster

Centrally Located Private Corner Unit

Holiday Rental House
1.9 kilometres from Cape Cod Rail Trail
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Newly updated, traditional townhouse with recently renovated bathrooms - a, holiday rental in Brewster
Newly updated, traditional townhouse with recently renovated bathrooms - a, holiday rental in Brewster
Newly updated, traditional townhouse with recently renovated bathrooms - a, holiday rental in Brewster

Newly updated, traditional townhouse with recently renovated bathrooms - a

Condo/Apartment
2.1 kilometres from Cape Cod Rail Trail
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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This spacious Billington Village condo features updated kitchen and 2 BRs plus, holiday rental in Brewster
This spacious Billington Village condo features updated kitchen and 2 BRs plus, holiday rental in Brewster
This spacious Billington Village condo features updated kitchen and 2 BRs plus, holiday rental in Brewster

This spacious Billington Village condo features updated kitchen and 2 BRs plus

Condo/Apartment
1.4 kilometres from Cape Cod Rail Trail
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Heart of Brewster .5 Miles to Beach!, holiday rental in Brewster
Heart of Brewster .5 Miles to Beach!, holiday rental in Brewster
Heart of Brewster .5 Miles to Beach!, holiday rental in Brewster

Heart of Brewster .5 Miles to Beach!

Holiday Rental House
1.4 kilometres from Cape Cod Rail Trail
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Ocean Edge Resort- Beautiful A-Style Townhouse with Pool Priveleges, holiday rental in Brewster
Ocean Edge Resort- Beautiful A-Style Townhouse with Pool Priveleges, holiday rental in Brewster
Ocean Edge Resort- Beautiful A-Style Townhouse with Pool Priveleges, holiday rental in Brewster

Ocean Edge Resort- Beautiful A-Style Townhouse with Pool Priveleges

Condo/Apartment
2.6 kilometres from Cape Cod Rail Trail
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy Cape Condo minutes from Brewster Beaches, holiday rental in Brewster
Cozy Cape Condo minutes from Brewster Beaches, holiday rental in Brewster
Cozy Cape Condo minutes from Brewster Beaches, holiday rental in Brewster

Cozy Cape Condo minutes from Brewster Beaches

Condo/Apartment
2.1 kilometres from Cape Cod Rail Trail
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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