Vacation rentals in Holliston

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Top-rated vacation rentals in Holliston

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Top guest favorite

A serene coastal view reveals a stone jetty extending into calm waters, dotted with sailboats. Lush greenery frames the foreground, while the distant landscape features a quaint town along the shoreline, under a clear blue sky with scattered clouds.

Home in Rockport

5 out of 5 average rating, 42 reviews

New South End Home Quiet Lane To Old Garden Beach

Newer furnished home, 1/2 mile walk to quaint Bearskin Neck with Rockport shops & galleries. Old Garden Beach 1/4 mile walk down a quiet unpaved lane. 3 BR/3 Bath home available for summer weekly vacations. Family friendly, 3 prkg spaces, 2 decks, new appliances (laundry, microwave & dishwasher), hardwood floors, new rugs & beds, full basement w/ pool table, fenced yard. Several beaches, hiking trails nearby or take a train to Salem, Newburyport, or Boston. Longer term winter rental available

Guest favorite

A serene outdoor seating area is surrounded by lush greenery, featuring two dark wooden chairs and a small table. A natural landscape includes a gently flowing brook nearby, with a weathered bench positioned to enjoy the peaceful view.

Home in Plymouth

4.82 out of 5 average rating, 325 reviews

Historic 1 Bed/In Town/Best Location/Hot tub/deck

PLEASE DO NOT BOOK WEEKENDS/HOLIDAYS/SUMMERS in advanced. I only use this 1 bed to fill gaps when the larger listing for this home isn't rented (mostly midweek) Beautifully restored historic home, directly in town, steps away from the Pilgrims 1st settlement, ocean, award winning restaurants, historic attractions, shops, nightlife, entertainment, tours,ferries, etc. Directly on the town brook/gristmill. Deck with view, firepit, hot tub, grill. Comfortable/clean/cozy bed, working wood stove.

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, 132 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

A sandy beach extends along a calm ocean, where gentle waves lap at the shore. Rocky formations are visible in the water, and a clear blue sky overhead enhances the serene coastal view.

Home in Scituate

4.95 out of 5 average rating, 21 reviews

Button Beach Cottage

Capture the breeze of the coast at Button Beach Cottage! •5 min walk to beach. •Brand new remodel. •Family friendly. •Oceanview balcony. •Luxury bunk room. •Dedicated workspace. •Outdoor dining area on spacious deck directly off kitchen. •Access to lifeguard beach Primary BR: king bed, TV, reading nook, ocean view & balcony. BR #2: queen bed, dedicated work space, ocean view & balcony. Bunk room: 5 twin beds with play space. Full bath on each floor. Tub, standing shower, washer & dryer.

Guest favorite

Cottage in Oakland Beach

4.98 out of 5 average rating, 145 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

Home in Falmouth

4.86 out of 5 average rating, 35 reviews

Cape Vacation in style! Close to Main St & Beaches

We affectionately call this house 'The Local,' as it sits in the heart of beautiful Falmouth, within short walking distance to the quaint Main St. shops, delectable restaurants, fish markets, entertainment like bowling and axe-throwing (!), and is a short drive to Woods Hole and many of the Cape's most breathtaking beaches along the coast. Great summer or off-season destination, the house is complete with high-end finishes and furnishings to make your vacation especially comfortable. Enjoy!

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, 218 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.

Top guest favorite

The modern kitchen features granite countertops and stainless steel appliances. Ample cabinetry provides storage, with a central wooden island offering additional workspace. Natural light enters through the window above the sink, highlighting the clean lines and functional layout of the space.

Home in Rockport

5 out of 5 average rating, 14 reviews

Adorable renovated house, steps from Front Beach

This charming home was recently fully renovated. The brand new kitchen features stunning granite countertops and stainless steel appliances. The large living/dining room features a 55" flat-screen TV comfy seatingnd a dining table for 4. There is a king bed in the Master Bedroom, along with a TV, ceiling fan, and air conditioning. The second bedroom has a twin daybed, with a second twin trundle bed underneath. The backyard features a patio with a seating for 4 and a gas grill.

Superhost

The image captures a serene beachfront with gentle waves lapping against sandy shores. Rocks line the edge of the beach, while a clear blue sky stretches overhead, merging with the tranquil sea. The distant coastline features various structures, enhancing the scenic view.

Home in Scituate

4.84 out of 5 average rating, 61 reviews

Sand Hills Barker Tavern RiverClub lighthouse -

Walking distance to sand hills beach - super close to BARKER TAVERN! One mile from center of town with restaurants and shops. Nearby basketball court. Grassy backyard . New furnishings new full bath and new mattresses. Freshly painted well maintained by owner bedrooms are upstairs. There is only one full bath upstairs Totally redone 2024. Bungalow beach style home. some guests find stairs to be “ steep” … my 82 year old mom does fine with the stairs and rail!

Top guest favorite

A harbor scene features numerous boats docked alongside wooden piers, with a small fuel dock prominently situated at the center. Lush greenery surrounds the area, and a soft, golden light fills the sky as the sun sets, creating a serene atmosphere.

Home in Scituate

5 out of 5 average rating, 20 reviews

Coastal Retreat

Welcome to our coastal rental, a charming retreat nestled in the heart of a vibrant beach town. With modern amenities and coastal decor, unwind in the light-filled spaces and savor beautiful marsh views from the well manicured backyard. Located about a mile from Main Street, you can walk or bike on the flat sidewalk to restaurants, shops and the harbor. Close by you'll also find a dog park, the beautiful public golf course, Widow's Walk and of course the beach!

Top guest favorite

An expansive deck is illuminated by soft outdoor lighting, featuring a gazebo and several comfortable seating options. The serene view of the bay is showcased under a twilight sky, displaying a gradient of colors ranging from deep blue to hints of purple.

Home in Fairhaven

5 out of 5 average rating, 21 reviews

Stunning Luxury House with Sunset & Private Beach

Luxury rental with unobstructed, breathtaking SUNSETS from the expansive deck that overlooks Buzzards Bay. Enjoy a Cape Cod experience without any of the traffic. Perfect for families, the private beach and fire pit area provide a relaxing place to splash, play and make memories. This oceanfront home is a few minutes from charming towns, such as Mattapoisett, Fairhaven, New Bedford, top-notch restaurants and the ferry to Martha's Vineyard and Nantucket.

Guest favorite

An aerial view of the lake house is presented, showcasing its two-story structure and surrounding wooden fence. The property is adjacent to the serene lake, with a clear view of the water and nearby trees, enhancing the natural setting.

Home in Plymouth

4.93 out of 5 average rating, 41 reviews

The Lake House Paradise!

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!