Vacation rentals in Upton

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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

SamanthaRating, 5 stars3 weeks ago

My family of six was extremely pleased with our stay at Dean’s property. He was incredibly responsive and helpful when I was having trouble making the reservation. The home was exactly as described. Very clean. Plenty of linens and towels. My kids loved the game room. Would definitely stay here again.

Guest favorite

Apartment in Winthrop

4.96 out of 5 average rating, 302 reviews

Cody's Place Boston Airport Pool/Beaches ParkFree

StephanieRating, 5 stars4 weeks ago

Frank went above and beyond to communicate check-in instructions, rules of the Air BnB, had all the thoughtful amenities for a slumbo! Definitely an ideal location for nicer weather with the location! Unfortunately the weather hindered the ability to fully enjoy this experience with the water so close! Would book again with better weather!!!

Guest favorite

Home in Scituate

4.95 out of 5 average rating, 21 reviews

Button Beach Cottage

DennisRating, 5 stars4 days ago

Courtney & Chris were amazing hosts! They went above and beyond to answer all our concerns prior to our stay regarding public transport to Boston for the marathon. The house was awesome, with the beach only blocks away. We had an excellent experience & we're so grateful for our hosts and this beautiful lodging.

Guest favorite

Cottage in Oakland Beach

4.98 out of 5 average rating, 144 reviews

Renovated cottage w water views and walk to beach

Emily DianaRating, 5 stars2 days ago

Angela and her husband Jim were very friendly, sweet helpful and very accommodating. I highly recommend staying at their house in the beautiful quaint beach neighborhood of Warwick. One thing that stood out was the house did not smell like heavy and scents. I am a stage three cancer survivor so I live a nontoxic lifestyle. I liked how the bath towels and the bedding And the furniture did not smell like heavy chemicals/scents for me and my toddlers. The house was clean, beautiful and so cozy. My toddlers had a blast, and it was hard for everyone to leave. 10/10. I’ve traveled the world and I’ve stayed at many Airbnb‘s I loved this house :)

Superhost

Cottage in Westford

4.92 out of 5 average rating, 37 reviews

Beach & pond cottage ! Westford MA and Boston!

MelanieRating, 5 stars6 months ago

We had an absolute blast on our girls getaway weekend!! The cottage and community were amazing, exactly what we were hoping for and Doug couldn't have been nicer or more helpful. He was always available by text or phone. The cottage was clean, nicely equipped, and a great location!! We will definitely be renting this cottage again on our next trip!!! Thanks for having us... we loved every minute!! 🧙🧙🧙

Superhost

Apartment in Swampscott

4.87 out of 5 average rating, 111 reviews

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

AnissaRating, 5 stars3 days ago

We absolutely loved our stay at Ryan’s place! The home was beautiful, spacious, and pristine—just like the photos. Ryan was a wonderful host from booking to check-out, making everything easy and welcoming. We especially loved the location, with the beach and great local restaurants just a short walk away. We would definitely stay here again!

Top guest favorite

Home in Fairhaven

5 out of 5 average rating, 21 reviews

Stunning Luxury House with Sunset & Private Beach

SerenaRating, 5 stars1 week ago

We wouldn’t hesitate to stay at Bill’s place again. The private beach was amazing. The views were stunning and the outside well well equipped with furniture. The house itself was beautiful. Updated and spacious. The kitchen had everything you could possible need for a gourmet meal. Sometimes when we rent houses, they are poorly equipped. Not this one. It was such a relief. The neighborhood was great and the next door neighbor was very friendly. The area has a lot of restaurants and stores, so everything is close by. Bill was very communicative and quickly responded to any inquiries. He was a great host. Honestly I have nothing bad to say.

Guest favorite

Home in Dartmouth

5 out of 5 average rating, 19 reviews

Unique Coastal Retreat: South Dartmouth, MA

JayRating, 5 stars7 months ago

What a wonderful stay! John is a welcoming and friendly host. We were in Dartmouth for bike rides and the beach, and John had great recommendations for local spots. The house is very cozy and full of books and local art and artifacts. The location is scenic and quiet, with great stargazing at night and birdwatching during the day.

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What guests are saying

Brand new! Whole apartment, huge tub, full kitchen

4.99 out of 5 average rating, 95 reviews1 week 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

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

4.98 out of 5 average rating, 60 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

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, 33 reviews2 days ago

This was my third time at Darryl’s‘s place and I will be back again. For the simple fact that if you need to be in the Beverly and Salem area this is a perfect location to post up and walk to everything you need. Or, drive if you must. There’s a train to Boston a couple blocks away.Darryl‘s place itself has everything you need to feel and operate like you’re at home. See you again soon, Darryl.

Apartment in Beverly

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Popular amenities for Upton vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Upton's top sights

Red Rock Grill and Bar7 locals recommend

Mendon Twin Drive-In6 locals recommend

Shaw's4 locals recommend

Other great vacation rentals in Upton

Guest favorite

Cottage in Portsmouth

5 out of 5 average rating, 8 reviews

Weathervane Cottage #4 of 8 in Portsmouth

ZacharyRating, 5 stars1 week ago

Great host and location. Was in town for the Newport Marathon and to visit a friend in Providence. Location was great and so was the cottage! Highly recommend staying here

Guest favorite

Home in Westminster

4.94 out of 5 average rating, 127 reviews

Wachusett Mountain Get-Away

DaeshaRating, 5 stars3 months ago

It was a pleasure staying here ! Everything is clean and the house is such a nice size !

Top guest favorite

Home in Andover

4.98 out of 5 average rating, 56 reviews

Spacious Classic Lakefront Home with jet tub

JeffreyRating, 5 stars3 months ago

The house felt like coming home. Everything you need was provided. The location is beautiful as is the surrounding area. We needed proximity to family and this was a perfect spot. All the amenities in the home were available and perfect for a weeklong stay. Thank you for a great stay!

Guest favorite

Home in Mattapoisett

4.86 out of 5 average rating, 7 reviews

5 Blocks to Beach+Town, Stocked Kitchen, Cozy Beds

DavidRating, 5 stars2 months ago

Caitlin was a wonderful hostess, and the house was very nice. I would definitely recommend if you were going to be in the area.

Top guest favorite

Apartment in North End

5 out of 5 average rating, 7 reviews

Beautiful and spacious lovely home

ChrisRating, 5 stars4 weeks ago

Place worked out perfect

Superhost

Apartment in Brighton

4.84 out of 5 average rating, 31 reviews

The Curie-Perfect for Monthly Stays

XuemeiRating, 5 stars1 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!

Superhost

Home in Worcester

4.85 out of 5 average rating, 119 reviews

COMFORTABLE 2ND FLOOR, FULL EQUIPPED&PET FRIENDLY

AnanthRating, 5 stars1 week ago

Dilsia is a great host. She provided lot of things thoughtfully which were extremely useful for us. We enjoyed our stay. She is very responsive and kind. Thank you for making our stay so nice.

Guest favorite