Upton Vacation Rentals from $121: Search Short-Term Rentals

Q: What's the top vacation rental that Upton has to offer?

Home Away from Home! : This vacation home rental near Upton offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a hot tub.

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Our top choices for Upton vacation rentals

Charming single family Cottage, pet friendly, close to Prov, Woon, MA & highways

Lincoln

Tyson P.

$179 nightly

Apr 16 - Apr 17

Total with taxes and fees

Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham

Framingham

Jenny S.

$191 nightly

Apr 16 - Apr 17

Total with taxes and fees

The Tree House at Underhill Hollow

Thompson

Patrice D.

$171 nightly

Apr 15 - Apr 16

Total with taxes and fees

SteamPunk Bunk House and Intergalactic Way Station

Thompson

Pauline S.

$166 nightly

Apr 15 - Apr 16

Total with taxes and fees

Wizard's Roost at Underhill Hollow

North Grosvenordale

Meghann H.

$166 nightly

Apr 27 - Apr 28

Total with taxes and fees

Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access

Framingham

Richard M.

$251 nightly

Apr 15 - Apr 16

Total with taxes and fees

1 bedroom, iron/ironing board, WiFi, bed sheets

The Studio-Suite at Putnam Pike NEW APT Near PVD

Johnston

$303 nightly

Apr 15 - Apr 16

Total with taxes and fees

Welcome in this charming one bedroom apartment located in Westwood. WorldCup2026

Westwood

$173 nightly

Apr 22 - Apr 23

Total with taxes and fees

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Top Upton Hotel Reviews

DoubleTree by Hilton Hotel Boston - Westborough

10/10 Excellent

"This was a very comfortable and clean hotel. Will definitely stay here again. "

Comfort Inn Auburn - Worcester

8/10 Good

"Decor is good, and property is Clean. Staff is Friendly and helpful. However, there were minor problems with amenities. For example, the reason why the coffee maker did Not work when I first tried to use it was because you have to Flip a master switch first--that nobody told me about nor did any sign. Had to get front desk to help with that. Also, TV controller is somewhat erratic. You often have to push a button multiple times and change pointing angle to increase volume or power on/off."

Best Western The Inn at Sharon/Foxboro

8/10 Good

"I enjoyed my weekend stay at this BW. I would have given it 5 stars except the road behind the hotel was noisey at night. Otherwise it was very clean and comfortable but the best was the buffet breakfast! The waiter kept refreshing and refilling the food. There was everything from eggs to waffles, cereals and fresh yogurt. "

enVision Hotel & Conference Center Mansfield-Foxboro

6/10 Okay

"Check-in was smooth. The hotel is in desperate need of a refresh. The hallways smell of smoke and mildew as the bathrooms in the guest rooms have water damage and has a damp odor. We spent two nights for a dance competition and while the ballroom area was fine for our purposes it would have been great to have a better experience with the restaurant/bar onsite as well as the pool area. The decor is lacking, no greenery/plants around the pool or general comforts in the lobby area to create an experience to hang out. "

Red Roof Inn Boston - Southborough/ Worcester

2/10 Terrible

"The property didn't feel safe, let alone friendly. The building is in terrible shape and the clientele is questionable. I felt uncomfortable immediately. When I go to the front desk (in a dark, smelly office) , the attendant told me he needed to change my room because I booked an accessible room and that there would be a room change charge. I agreed to that, but then the total charge was significantly higher than what I booked . Because he "had to" change my room, he did not have to honor the price when I initially booked through Expedia. Another person sitting in the office told me that the desk attendant did the same thing to him. I ended up leaving and staying at a different hotel. I almost never leave reviews but this experience was so awful. I don't understand how this place has so many stars. "

Find out more about Upton

Everything you need to know about Upton vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Upton vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Upton vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Upton vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Upton. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Upton in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $121 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Upton rentals

At Expedia, we put the best Upton vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Upton rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Upton vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Upton. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Frequently asked questions

Can I find vacation rentals in Upton?

Yes, there are vacation rentals near popular points of interest in Upton, or you can choose a more secluded option if you're looking for a relaxing stay.

What's the top vacation rental that Upton has to offer?

Home Away from Home!: This vacation home rental near Upton offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a hot tub.

What’s there to see and do in Upton?

While exploring the area, visit family-friendly sights like Southwick's Zoo, or get outside and enjoy nature at Dean Pond. In the larger area, you’ll find Hopkinton State Park and Cummings School of Veterinary Medicine at Tufts University.

What’s a vacation rental in Upton like?

Vacation rentals are privately owned properties you can stay in for a long or short time in Upton. Vacation rentals offer amenities like WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of safety away from public hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for small groups.

Upton Vacation Rentals

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Check prices for these dates

Our top choices for Upton vacation rentals

Charming single family Cottage, pet friendly, close to Prov, Woon, MA & highways

Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham

The Tree House at Underhill Hollow

SteamPunk Bunk House and Intergalactic Way Station

Wizard's Roost at Underhill Hollow

Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access

The Studio-Suite at Putnam Pike NEW APT Near PVD

Welcome in this charming one bedroom apartment located in Westwood. WorldCup2026

Charming 3-bedroom house in delightful Ashland for your getaway

Charming 1-bedroom apartment with AC, WiFi in pleasant Webster

Beautiful Worcester Downtown King Bd/Office World Cup Boston

Private Luxury 2 Bedroom Suite

Spacious 4BR Family Home in Worcester near Parks 16/2

totally remodeled house with fitness room, close to Boston and Worcester

Lakefront Cottage 2 Mi to Palladium in Worcester!

Beautiful family getaway, walking distance to markets, 35 min drive to Boston

Zen Inspired Retreat with Private Forest Trails

Spacious 4-bedroom with four and half bathrooms

Cozy Adventure Filled Escape Free Parking 2 Bedroom Apts

Spacious Getaway by TreeHouse Brewery & Amazon WareHouse

Find vacation rentals that suit your style

Top Upton Hotel Reviews

DoubleTree by Hilton Hotel Boston - Westborough

Find out more about Upton

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