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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Top guest favorite

Home in Mattapoisett

4.94 out of 5 average rating, 192 reviews

*The Cozy Escape* | Historic South Coast Retreat

SAVE (heart) US NOW! Escape to Mattapoisett on the South Coast of MA & experience the charming beauty of this small town! Our recently updated home is a perfect retreat for your getaway. Take in the stunning views of the harbor at Shipyard Park or stroll along the area beaches. Explore the area's history at Neds Point Lighthouse & Salty the Seahorse. Unwind at our cozy & inviting home. Dine in with our fully equipped kitchen or indulge at the many great restaurants! Book your unforgettable stay!

Guest favorite

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, 302 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, 181 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, 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 Oakland Beach

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

Cottage in Westford

4.92 out of 5 average rating, 36 reviews

Beach & pond cottage ! Westford MA and Boston!

Summer Village resort is only 20 miles from Boston. Best of both worlds! Your New England style cottage is steps to the beach, Lodge restaurant & bar, heated pools (family & adult), hot-tub, playground, tennis/ basketball/ fire pits pocket parks, golf putt, fishing, 24-hr fitness center. You'll enjoy lake views of Long Sought for Pond from the sun-filled porch, sandy beach, nestled in a beautiful gated seasonal cottage community. CENTRAL A/C !! Queen beds, Bunk bed. Weber outdoor grilling.

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, 108 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, 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.

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, 23 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!

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What guests are saying

Brand new! Whole apartment, huge tub, full kitchen

4.99 out of 5 average rating, 94 reviews4 days ago

Jennifer's home is perfect! From the lovely entrance to the interior of the home, everything is exactly as described in the listing. The bed is super comfortable and you will definitely get a good night's sleep there. The kitchen has everything you need to cook a meal and there is a lovely area outside to eat if you wish. The bathroom is beautiful and the shower has amazing water pressure. Basically a nice home away from home. I would recommend this place to anyone. We will definitely book again when in the area.

Apartment in Mattapoisett

What guests are saying

Lovely Day Oceanside

4.93 out of 5 average rating, 28 reviews3 months ago

"Lovely Day" was the perfect getaway we were hoping for. The place looked exactly like the photos showed: beautiful sun-filled front-room, nice spacious kitchen with an open concept, and the easiest access to a private beach. The place had two bedrooms (one with a queen-sized bed and one with a bed bunk) and a bathroom (with washer and dryer), so it's perfect for a family or a small group of friends. Maybe because it was winter but we were the only ones around, which made our time at the beach even that more enjoyable. Fairhaven is about 10mins away with enough services and restaurants, although we brought everything with us so that we wouldn't have to rely on those. Do note that the exterior and interior walls are a little thin, in case you're sensitive to noise. Overall, a wonderful and peaceful retreat.

Home in Fairhaven

What guests are saying

Village Colonial with Cohasset Harbor Views

4.91 out of 5 average rating, 32 reviews3 weeks ago

This is a beautiful and spacious home with New England charm and in a great location. The house looks exactly as pictured and was spotless. The rooms were well appointed with lots of space to sit and relax. It’s perfect for visiting this beautiful area of MA. Michael is a responsive and helpful host and very considerate of his guests. We would absolutely stay again and can highly recommend this home for your stay. Five star all the way.

Home in Cohasset

What guests are saying

Cottage @ Partridge Pond

5 out of 5 average rating, 59 reviews2 months ago

Todd was so great to work with. Extremely responsive and helpful! His place was so cute, very clean and very well appointed. It has everything you could ever need and very organized. We rented it to ski at Wachusetts and it was great location( only 15 mins away). We would rent again. Thank you!

Cottage in Westminster

What guests are saying

Lakefront Home With a Great Views for Every Season

5 out of 5 average rating, 14 reviews4 months ago

We traveled up from Florida to visit family in RI & MA for Thanksgiving and stayed in the lake house. After a very long drive, it was so lovely checking in to a bright, clean, peaceful house. Everything is brand new and well appointed. Jolene was so responsive on the week leading up, flexible with our arrival time and had great local recommendations. After we arrived she stopped by with flowers to welcome us. We lived in Rhode Island for 40 years and I had never been to that area of the state before! While it feels like a peaceful retreat, the little village center is about 2 miles away and has grocery, cvs, Dunkins, and a brewery among other things. We also drove a few minutes further to one of the oldest country stores in America. The fire pit was fun for the kids to make s’mores and we enjoyed playing all of the games every night. It was a great Airbnb stay and we will definitely be back again to enjoy it in the warmer weather!

Home in Burrillville

What guests are saying

The Curie-Perfect for Monthly Stays

4.84 out of 5 average rating, 31 reviews1 week ago

This apartment is a great find! The location is perfect, not far from Boston, near every colleges for those who come visiting! This apartment building is indeed very new, built in 2021; but also blended in with history, the leasing office/lobby was converted from an old day chapel, pristine, elegant. Very unique Airbnb experience indeed. The small town is full of vibe with various kinds of cuisines, very good for families, young or old. Melissa, the host is super, giving us very detailed information and instructions from parking to checking in, every tiny details she thoughtfully considered. We couldn’t be happier to stay in this apartment. Highly recommended!

Apartment in Brighton

What guests are saying

Every room a water view updated kitchen & bath

4.95 out of 5 average rating, 21 reviews3 months ago

Excellent experience. Easy check in and the place was perfect, she even had some snacks waiting for us upon arrival. Easy walk to the ferry into Boston, and easy parking. It was winter, but there were plenty of outdoor activities so we'd love to come back during the summer. Older house but so charming and great location. Overall great communication before, during, and after; she even offered to ship a shoe my niece left behind to us. Would love to come back and would absolutely recommend to anyone looking for a great place in Hull.

Home in Hull

What guests are saying

#1 Top Flr Waterview|Lux Design|Pvt Balcony

5 out of 5 average rating, 32 reviews1 week ago

Darryl’s place is in a perfect location to easily walk around Beverly and with a car access Salem and the surrounding area. There’s also a train within walking distance and quick access to Boston. Darryl‘s place itself is definitely a home away from home with everything you need to be comfortable. Darryl himself is immediately responsive and has great local tips. Looking forward to staying again!

Apartment in Beverly

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