128+ Vacation Rentals Near Waskosim's Rock Reservation |
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  4. Waskosim's Rock Reservation

Whispering Pines Cottages - Vacation Rentals in Waskosim's Rock Reservation

Menemsha Home Fully Renovated w/Amazing Waterview's of Vineyard Sound From US $1,056
         

10.0 (17 Reviews)
House
Menemsha Home Fully Renovated w/Amazing Waterview's of Vineyard Sound
  • Air Conditioner
  • Parking
  • TV

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Hillside Oak From US $914
         

10.0 (1 Review)
House
Hillside Oak
  • Pet Friendly
  • Wheelchair Accessible
  • Balcony/Terrace

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Chilmark 1-bedroom Bunk house, WiFi, AC. Private Beach, Pets. No kitchen From US $1,403
         

New
House
Chilmark 1-bedroom Bunk house, WiFi, AC. Private Beach, Pets. No kitchen
  • Air Conditioner
  • Parking
  • TV

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Bright and cozy menemsha cottage From US $682
         

10.0 (5 Reviews)
Cottage
Bright and cozy menemsha cottage
  • Air Conditioner
  • Parking
  • Pet Friendly

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The Eliot Noyes From US $1,895
         

|
9.0 (1 Review)
House
The Eliot Noyes
  • Air Conditioner
  • Pool
  • View

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Secluded retreat in Seven Gates Farm on 7 Acres, Private Beach, Tennis, Pond From US $1,053
         

10.0 (6 Reviews)
House
Secluded retreat in Seven Gates Farm on 7 Acres, Private Beach, Tennis, Pond

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Historic Captains House - Newly Renovated Primary Bathroom and Upgraded Kitchen From US $782
         

10.0 (57 Reviews)
House
Historic Captains House - Newly Renovated Primary Bathroom and Upgraded Kitchen
  • Air Conditioner
  • Parking
  • TV

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Chilmark Guest House From US $749
         

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8.6 (6 Reviews)
House
Chilmark Guest House
  • Air Conditioner
  • Pet Friendly
  • View

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Unwind in Guest House overlooking Menemsha Pond. Dogs ok+ Lv-2 EV charger. From US $524
         

10.0 (57 Reviews)
House
Unwind in Guest House overlooking Menemsha Pond. Dogs ok+ Lv-2 EV charger.
  • Air Conditioner
  • Parking
  • Pet Friendly

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Menemsha Pond views & access! Mid-century renovated beach house. Dogs welcome. From US $412
         

10.0 (29 Reviews)
House
Menemsha Pond views & access! Mid-century renovated beach house. Dogs welcome.
  • Air Conditioner
  • Parking
  • Pet Friendly

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Light Open Vacation Home, Sweeping Waterviews, Hill Top, Private From US $1,967
         

10.0 (9 Reviews)
House
Light Open Vacation Home, Sweeping Waterviews, Hill Top, Private
  • Air Conditioner
  • Parking
  • TV

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Post and Beam home with westward views of the ocean and sunsets From US $1,362
         

10.0 (8 Reviews)
House
Post and Beam home with westward views of the ocean and sunsets
  • Air Conditioner
  • Parking
  • Pet Friendly

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Lovely Chilmark home on Abel's Hill with private beach, pond, tennis, and trails From US $1,335
         

10.0 (7 Reviews)
House
Lovely Chilmark home on Abel's Hill with private beach, pond, tennis, and trails
  • Air Conditioner
  • Parking
  • TV

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Peaceful Chilmark Farmhouse by Menemsha Beach From US $569
         

10.0 (6 Reviews)
House
Peaceful Chilmark Farmhouse by Menemsha Beach
  • Air Conditioner
  • Parking
  • TV

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The Field House - Peaceful Martha’s Vineyard Escape with Serene Field Views From US $1,109
         

10.0 (3 Reviews)
House
The Field House - Peaceful Martha’s Vineyard Escape with Serene Field Views
  • Air Conditioner
  • Parking
  • TV

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Peaceful Scenic Up-Island Retreat With Private Martha's Vineyard Beach From US $802
         

10.0 (1 Review)
House
Peaceful Scenic Up-Island Retreat With Private Martha's Vineyard Beach
  • Parking
  • Security/Safety
  • Bedding/Linens

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Private Hillside Home, Fully Equipped Kitchen, Dog-Friendly, A/C, W/D From US $1,168
         

9.6 (9 Reviews)
House
Private Hillside Home, Fully Equipped Kitchen, Dog-Friendly, A/C, W/D
  • Air Conditioner
  • Pet Friendly
  • TV

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Amazing sunsets, a welcoming home, and island adventures. Lifetime memories! From US $2,113
         

New
House
Amazing sunsets, a welcoming home, and island adventures. Lifetime memories!
  • Air Conditioner
  • Parking
  • TV

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Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks From US $831
         

New
House
Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks
  • Air Conditioner
  • Pool
  • TV

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Cozy 3BR Cottage with Lambert's Cove Beach access From US $755
         

New
Cottage
Cozy 3BR Cottage with Lambert's Cove Beach access
  • Air Conditioner
  • Parking
  • Pet Friendly

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Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches From US $611
         

New
House
Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches
  • Air Conditioner
  • Pet Friendly
  • TV

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2-bedroom cottage in Chilmark 1/2 mile from Menemsha Harbor and fishing village From US $358
         

New
Cottage
2-bedroom cottage in Chilmark 1/2 mile from Menemsha Harbor and fishing village
  • Air Conditioner
  • Parking
  • TV

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Charming Chilmark beach house with private Abel's Hill beach access From US $1,519
         

9.8 (11 Reviews)
House
Charming Chilmark beach house with private Abel's Hill beach access
  • Air Conditioner
  • Parking
  • TV

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Charming Rustic Cottage From US $413
         

10.0 (9 Reviews)
Cottage
Charming Rustic Cottage
  • Parking
  • TV
  • View

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★ Pro Tip: Whisperingpinescottages makes it easy to compare the best listings on Whisperingpinescottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Whisperingpinescottages homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Waskosim's Rock Reservation.

Weather in Waskosim's Rock Reservation

View the weather forecast for Waskosim's Rock Reservation before booking your Waskosim's Rock Reservation Vacation Rentals to confirm your best time to go.

December - February
High 46°F       Low 21°F
March - May
High 66°F       Low 25°F
June - August
High 81°F       Low 55°F
September - November
High 76°F       Low 33°F

Top Attractions Around Waskosim's Rock Reservation, MA

Whisperingpinescottages offers a large selection of top attractions around Waskosim's Rock Reservation. Research things to do on your vacation before you visit Waskosim's Rock Reservation.


Oak Bluffs Harbor Inkwell Beach Katama Beach Woods Hole Ferry Terminal Edgartown Lighthouse Oak Bluffs Town Beach Nobska Lighthouse Martha's Vineyard Film Center Cape Cod Beaches South Beach Martha's Vineyard Museum Martha's Vineyard Chamber of Commerce Woods Hole Oceanographic Institution Flying Horses Carousel Lighthouse Beach Island Cove Miniature Golf Gus Ben David's World of Reptiles and Birds Park Martha's Vineyard Preservation Trust Historic Buildings Chilmark Chocolates Vineyard Haven Public Library

Waskosim's Rock Reservation Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Waskosim's Rock Reservation?

There are a lot of options in Waskosim's Rock Reservation. If you plan on staying in the Waskosim's Rock Reservation area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Waskosim's Rock Reservation:

How many vacation rentals are available in Waskosim's Rock Reservation?

Currently, the total number of properties listed in 2026 is over 128 in the Waskosim's Rock Reservation area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Waskosim's Rock Reservation.