Places to stay near Cherry and Webb Beach

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Top-rated vacation rentals near Cherry and Webb Beach

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Top guest favorite

The historic property is displayed from the street level, showcasing its architectural charm with a multi-story design. A covered porch is visible, featuring ornate woodwork. Shops line the street, contributing to a lively town atmosphere. Clear skies and bright sunlight enhance the inviting appearance.

Apartment in Oak Bluffs

4.92 out of 5 average rating, 109 reviews

Absolute Best Location on the Island

Ideal location for visitors in the middle of the most lively, diverse, fun town on Martha's Vineyard. This property is certified by the United States Department of Interior as a National Historic Property. The ferry terminal, restaurants, shops, markets, harbor, historic sites, entertainment, public transportation, and a clean sandy beach are all within minutes. A vehicle is not necessary. IF UNAVAILABLE: SIMILAR WALKABLE SISTER PROPERTY in Vineyard Haven: https://www.airbnb.com/rooms/49016488?

Guest favorite

A spacious front porch features comfortable gray seating arranged around a fire pit. String lights are installed above, adding warmth. Lush greenery can be seen in the surrounding landscape, with a view of the quiet road and neighboring properties.

Cottage in Mashpee

4.95 out of 5 average rating, 345 reviews

★The Islander | Steps From Water, Fire Pit, AC★

A pristine island getaway. This tastefully decorated cozy cottage is nestled in the Wild Life Sanctuary of Monomoscoy Island. The home is steps from the water with a small water access at the end of the road. The location is great for a family vacation, couples getaway or romantic retreat. You will be minutes from South Cape Beach, New Seabury and the Mashpee Commons. Relax on the large front porch that offers a fire pit and views of the water on either side. Stay with us on your next vacation!

Guest favorite

Home in Mashpee

4.94 out of 5 average rating, 110 reviews

Newly Renovated! Seconds to sand, fire pit, A/C

Recently Renovated! This Cape Cod Cottage is completely refreshed top to bottom. Less than 60 seconds to the sand. Cape cod vacations do not get any better than this! Located on idyllic Monomoscoy Island known for its gorgeous wildlife and stunning waterways, our home is the perfect choice to rent on Cape Cod. We are less than 10 Mins to Mashpee Commons and famous Mashpee Town Beach, Less than 5 mins to New Seabury and the Popponesset Inn, and only 15 mins to downtown Falmouth. Linens included!

Guest favorite

A wooden deck overlooks Johnson's Pond, with a table at the center surrounded by four chairs. Two red cushioned rocking chairs provide a comfortable seating option, and a vibrant red umbrella offers shade. Lush green trees frame the serene water view.

Home in Coventry

4.86 out of 5 average rating, 131 reviews

Awesome 3 bed vacation lake house. Great location!

Three bedroom house right on Johnson’s Pond with private water access right in the back yard. House features queen master with deck overlooking the pond. 2nd bedroom features a full bed with twin bunk bed above along with a stand alone twin bed. 3rd bedroom has a queen bed. Perfect for one or two couples to share. Full kitchen and laundry along with WiFi and streaming services. Use of 2 kayaks and pedal boat. Just two miles from I-95, so everything in southern New England is just minutes away!!

Guest favorite

Cottage in Warwick

4.98 out of 5 average rating, 142 reviews

Renovated cottage w water views and walk to beach

This beautiful cottage has waterviews from most rooms. 1st floor has 4 season porch, Living room opens to white kitchen w quartz countertops, dining area , bedroom and 1/2 bath. 2nd floor has 2 bedrooms & full bath with laundry. Outdoor sitting at Small table in the front garden & Adirondack chairs in the backyard. 1/2 block to the beach, kayak, fishing, boat launch, cafe & 2 restaurants. Home has been renovated w love and caring. No parties. Please be considerate of cleaning person.

Superhost

A colorful little free library stands on a wooden post, featuring a blue and white exterior with decorative trim. The glass door showcases a collection of books neatly arranged inside, inviting passersby to take or leave a book.

Cottage in Oak Bluffs

4.91 out of 5 average rating, 199 reviews

Best location!!! Beach & Town 5min walk 113R

Amazing! Walk to all Oak Bluffs has to offer. 5-10 minutes to harbor, town, beach and restaurants spectacular location! This property offers a private patio along with all the amenities. Beautiful landscaping. It is private and well appointed. 2 flat screen Televisions, wifi, appliances, tile throughout, granite counters, outdoor shower, gas grill and best of all it's all new. This 500 square foot unit will provide you with an excellent home base to explore Oak Bluffs and Martha's Vineyard.

Superhost

A tranquil shoreline is depicted, featuring gently sloping grass leading to a calm body of water. Soft ripples reflect the blue sky and fluffy clouds. In the distance, a house is visible, framed by the natural landscape.

Cottage in Fairhaven

4.83 out of 5 average rating, 217 reviews

Cottage by the Bay

Cottage in Fairhaven, perfect for a vacation for a small family, a romantic getaway or a home away from home if you are in the area for business. Enjoy all a vacation has to offer. During warmer weather, walk to the public beach and boat ramp - swim, sun, boat. Spend evenings by the outdoor fireplace. When it is cold out side, enjoy parks, museums, arts and cultural events, with evenings spent enjoying hot chocolate in front of the gas stove as the fire blazes providing a cozy warmth.

Guest favorite

An aerial view captures the collection of coastal cottages, surrounded by greenery and amenities. A spacious parking area is visible in the center, with cottages arranged neatly around it. A pool can be seen in the background, enhancing the community vibe of the area.

Bungalow in Middletown

4.83 out of 5 average rating, 106 reviews

Ellery Beach Bungalow #43– Walk to Beaches & Bites

The Ellery Beach Bungalows are a collection of 5 coastal cottages, each offering a refined yet relaxed setting for exploring Aquidneck Island. Stroll to nearby cafés, restaurants, and shoreline escapes, or reach Newport’s celebrated dining, boutiques, and historic landmarks in 5 minutes by car. Each bungalow includes its own private patio, ideal for unhurried evenings outdoors, and sits just a 1/4 mile from the beach, placing the island’s best experiences within easy reach.

Guest favorite

Home in Plymouth

4.93 out of 5 average rating, 41 reviews

Lakefront Scenic: Your Perfect Getaway!

Escape to our serene lake house with breathtaking views & endless opportunities for outdoor adventure. With a dedicated workspace, stay connected while enjoying tranquility. Take a paddle on the lake with kayaks & pedal boat, or relax on the patio with outdoor fire pit. Fully furnished & decorated, feel at home cooking in the fully equipped kitchen or curling up in the cozy living room. Book your stay today and experience the magic of nature firsthand!

Guest favorite

Apartment in Newport

4.99 out of 5 average rating, 329 reviews

The Peaceful Puffin

Great location, cleanliness and exceptional amenities are some of our strongest traits. This spotless apartment is located in a desirable part of the city, in walking distance to downtown, beaches, the mansions, restaurants, the harbor and Fort Adams! Fully equipped for a wonderful vacation! Central air & laundry in unit! 2 bedrooms, equipped with luxurious bedding, a spacious open living room with a beautifully updated kitchen and a large bathroom.

Superhost

Home in Edgartown

4.91 out of 5 average rating, 54 reviews

Updated Beautiful Cottage in Edgartown AC

A true island charmer. Light, airy and central-air-conditioned home offers all the comforts of modern living centrally located in Edgartown. Recently completed extensive upgrades completed enhance all of the space, including a new kitchen, both bathrooms, basement, and more. A spacious outdoor furnished deck with enclosed outdoor shower and an expansive grassy lawn make for a great space to relax. Great location makes Island travel a breeze.

Superhost

A well-maintained grassy area is surrounded by various shrubs and trees. The view extends to a serene body of water framed by lush greenery, under a clear blue sky with scattered clouds.

Guesthouse in Dartmouth

4.89 out of 5 average rating, 130 reviews

Lovely Lakeside Cottage

Keep it simple at this peaceful and centrally-located cottage. Lovely lakeside cottage with open floor plan. Centrally located in southeastern Massachusetts with short drives to Boston, Providence, Newport, and Cape Cod. Several beaches within 20 minutes. Washer/ Dryer on site and California King Size bed. A simple five (5) minute ride to UMass Dartmouth. Cottage has a living room, full kitchen, bedroom, full bath, and small dining area.