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Westport Vacation Rentals

1 - 23 of 23 rentals
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Orleans Oyster Shell - Orleans, MA Vacation Rental

Orleans Oyster Shell

Orleans, MA
3 Bed 2 Bath Sleeps 10
130 130 190 190 135 135 135 135 135 195 195 135 135 135 135 135 195
 Camp Out Cottage on White Island Pond - Wareham, MA Vacation Rental
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Seaside Park Cottage - Barnstable, MA Vacation Rental

Seaside Park Cottage

Barnstable, MA
3 Bed 2 Bath Sleeps 8
155 155 185 185 165 165 165 165 165 195 195 165 165 165 165 165 195
Seaview Condo at the Pagodas  - Provincetown, MA Vacation Rental
- - - - - - - 85 90 120 120 90 90 90 90 90 120
Bay Side Beauty in Eastham - Eastham, MA Vacation Rental

Bay Side Beauty in Eastham

Eastham, MA
4 Bed 2.5 Bath Sleeps 8
- - - - - - - - - - - - - - - - -
The Sea Chest  in The South of Chatham  - Chatham, MA Vacation Rental
- - - 120 115 115 115 115 115 160 150 - - - - - 150
Escape in Dennis - Dennis, MA Vacation Rental

Escape in Dennis

Dennis, MA
3 Bed 2 Bath Sleeps 7
- - - - - - - - - - - - - - - - -
Bayside Cape Codder - Dennis, MA Vacation Rental

Bayside Cape Codder

Dennis, MA
3 Bed 2 Bath Sleeps 8
115 115 150 150 120 120 120 120 120 160 160 120 120 120 120 120 160
The Place to be... - Provincetown, MA Vacation Rental

The Place to be...

Provincetown, MA
2 Bed 1 Bath Sleeps 5
90 99 140 140 99 99 99 115 99 - - 99 115 115 115 115 160
Couple's Paradise by the Sea - Chatham, MA Vacation Rental
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Chic Antique in Wellfleet Village - Wellfleet, MA Vacation Rental
125 125 165 165 130 130 130 135 135 180 180 135 135 135 135 135 180
Harwich Port Perfection - Harwich, MA Vacation Rental

Harwich Port Perfection

Harwich, MA
3 Bed 2.5 Bath Sleeps 8
90 - - 115 115 115 115 115 115 155 155 115 115 115 115 115 155
Shady Centerville Tree House - Centerville , MA Vacation Rental

Shady Centerville Tree House

Centerville , MA
4 Bed 2.5 Bath Sleeps 8 (6 Adults Max)
215 215 245 245 225 225 225 175 175 225 225 175 175 175 175 175 225
The Waterfront Penthouse - Provincetown, MA Vacation Rental
90 - - - - 99 115 130 130 185 185 130 130 130 130 125 -
The Boat House on The  Bass River  - Dennis, MA Vacation Rental
99 99 130 130 99 99 99 99 99 135 135 99 99 99 99 99 135
A Chatham Pearl on Oyster River - Chatham, MA Vacation Rental
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Nauset Beach Buddy  - Orleans, MA Vacation Rental

Nauset Beach Buddy

Orleans, MA
2 Bed 1 Bath Sleeps 4
- - - - - - - - - - - - - - - - -
The Beachcomber - Dennis, MA Vacation Rental

The Beachcomber

Dennis, MA
3 Bed 1 Bath Sleeps 7
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Nauset Beach Dream - Orleans, MA Vacation Rental

Nauset Beach Dream

Orleans, MA
3 Bed 1 Bath Sleeps 6
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Hyannis Port Haven - Hyannis, MA Vacation Rental

Hyannis Port Haven

Hyannis, MA
4 Bed 3 Bath Sleeps 7
- - - - - - - - - - - - - - - - -
Billingsgate Landing at Wellfleet Harbor - Wellfleet, MA Vacation Rental
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Waterview Chatham Home  - Chatham, MA Vacation Rental

Waterview Chatham Home

Chatham, MA
2 Bed 1.5 Bath Sleeps 7
- - - - - - - - - - - - - - - - -
Toes In The Sand at Craigville Beach - Centerville , MA Vacation Rental
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About Westport

Our Westport vacation rentals offer a quiet and restful spot for a relaxing getaway! Named for its position as the westernmost section of the original Massachusetts Bay Colony, today, Westport, Massachusetts enjoys a reputation for tranquil bay beaches and friendly locals, and as an ideal place to retire.

Where is Westport, MA? 

The town sits on Buzzards Bay, abutting New Bedford to the east and the state of Rhode Island to the west. Westport sees an influx of hundreds of tourists every summer who crave its small town appeal and pristine coast.

Things to Do in Westport

Westport may be small, but still reels visitors in every year thanks to its outdoor activities, historic sites, and small but thriving arts community. Mass Audubon's Allens Pond Wildlife Sanctuary is a more than 600-acre protected area encompassing beaches, ponds, and marshland. The sanctuary includes three trailheads, more than 300 bird species, and rare butterflies in a preserved garden. Swim to your heart's content at Horseneck Beach State Reservation, a two mile stretch of sandy beach that's popular with windsurfers and swimmers of all levels, and draws nature lovers to its estuary habitats and salt marshes.

Westport is home to several historic sites, including Handy House and Bell School. Handy House is an architectural marvel devoid of furnishings but filled to the brim with ever-evolving history. You can examine its transformation from an 18th-century structure to a Georgian abode to its present-day Federalist incarnation. Bell School is home to the Westport Historical Society, and was originally a 19th-century Greek Revival school for residents west of the Westport River. 

Visit Westport Town Farm to admire livestock, a vintage farmhouse, dairy barn, corn crib, and Colonial-era stone walls. Admire the view on the mile-long trail that loops along the river and through fields and pastures.

Galleries abound in this artists' colony. Check out the Westport Art Group, Dedee Shattuck Gallery, and Sticks Stones and Stars for paintings by local artisans.

Founded in 1986, Westport Rivers Winery boasts sparkling, table, and dessert wine to please any palate. If beer is more to your liking, Buzzards Bay Brewing crafts award-winning IPAs, porters, and red ales. 

Day Trips from Westport

Situated on the border of Rhode Island, Westport is your entry to all Massachusetts has to offer. Head to Boston or Salem, only 62 and 86 miles away, respectively. Cape Cod is only 50 miles away and you can enjoy myriad coastal towns, both quaint and hip. Martha's Vineyard is less than 80 miles away, via car and ferry. 

From hiking and biking trails to estuaries and butterfly habitats, Westport is sure to appeal to a variety of visitors. Our Westport vacation rentals are the perfect base from which to explore this charming city on Buzzards Bay!

Photo credit: Psalm25 via Shutterstock

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