Vacation rentals in Upton

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Upton

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Superhost

Vacation home in Natick

4.87 out of 5 average rating, 109 reviews

Private Lakefront with game room/Newly renovated

Ideal private location on crystal clear Lake Cochituate! Peaceful quiet spot w amazing view only 20 min to Boston & 1 or 2 min drive to anything u could need Fun game room &free use of tandem kayak & paddleboard and fishing Sliding barn door separates main king bedroom, bath, & open kitchen & livingroom from the back 2 queen beds, game room & bath Im always available to answer questions + provide tips, but I also respect your privacy & want u to feel comfy & independent 》25 6 person 3 car limit

Guest favorite

Apartment in Winthrop

4.96 out of 5 average rating, 305 reviews

Cody's Place Boston Airport Pool/Beaches ParkFree

Retreat, relax, & refresh in your own private entry basement in law apartment of our well bunkered Beach House. BEST LOCATION across from the mighty Atlantic & Iconic Winthrop Arms Hotel/Restaurant. Take in the salty air & breathtaking sunrises. Steps from Ocean Sunrise & Sandy Beach Surf. Walking distance to public transport, restaurants, parks, or Uber/Walk to the center bars & other attractions. Vacation living. Ferry minutes to downtown Boston. 1 of 3 officially licensed AirBnB's in town.

Guest favorite

Home in Westminster

4.9 out of 5 average rating, 182 reviews

Lakefront, view of ski mtn, fireplace, sauna

Direct lakefront with panoramic views of Wachusett Mountain (#1 skiing in MA). In the summer, enjoy the kayaks, canoe, paddle-boards, motor boat. In the winter, cozy up next to the fireplace and enjoy a complimentary bottle of wine. In the fall, gaze upon the breathtaking foliage from the sunroom. Outdoor shower, dock, firepit, hammock, bike, washer/dryer, desk, sauna, dishwasher, linens, kitchen amenities. Our other lakefront house is down the road: www.airbnb.com/h/lakefrontmountainview

Guest favorite

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!!

Top 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.

Guest favorite

Home in Fairhaven

4.93 out of 5 average rating, 106 reviews

Cozy Beach House with 270° Spectacular Views

Enjoy your getaway at our elevated beach house, the Fairhaven Seaside Retreat! Named one of Fodor's Top Ten Airbnbs for Socially Distanced Getaways in 2020 for its seclusion, stunning views, and easy access to many of New England's vacation spots, our home is perfect for adventurous vacations, quiet retreats, or remote working. Featuring 270 degree views that include the Atlantic ocean and a protected state marsh, our cozy home is also close to local restaurants, grocery stores, and shops.

Superhost

Apartment in Swampscott

4.87 out of 5 average rating, 111 reviews

Ocean views, Large Deck, Grill, Kid/Dog Friendly

The product of a complete gut renovation in 2020. The unit is 300 yards to Fisherman's Beach at the bottom of the street. The apartment is the 1st floor of a two family home (our family lives upstairs). It consists of 2 bedrooms, 2 full baths, pro kitchen, open living/dining area. The driveway can fit 2 cars (tight). There is additional parking at the bottom of the street. Please see house rules settings for holiday minimum bookings. We are pet friendly, but require case by case approval.

Superhost

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

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.

Superhost

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.

Top guest favorite

Home in Mattapoisett

5 out of 5 average rating, 25 reviews

Salty by the Sea

Bright and charming home with the perfect gathering space...large, open-concept great room with water view. Ideal location just a few-minutes walk to historic lighthouse, town beach and quaint seaside village! Nearby bike path for scenic coastal rides. New heating and A/C for year-round comfort, outdoor shower and many more amenities. Picture-perfect rental for a quiet getaway or whole-family fun! We hope to welcome you soon!

Guest favorite

Home in Smithfield

4.97 out of 5 average rating, 143 reviews

Luxury Home | Fire Pit | Beach | Grill | 2 Decks

Welcome to Stillwater.House - a custom built Airbnb. Our premier luxury home is situated overlooking a picturesque running river and 92 acre pond. Built in 2020, this beautiful 2,600 sq ft, five bedroom, four bath home boasts breathtaking views, nestled in the picturesque Georgiaville Village. Enjoy the views on TWO decks with plenty of outdoor seating, couches and a brand new gas grill! RE.02492-STR