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Upton Vacation Rentals

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Upton vacation rentals

Dining

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

Beautiful family getaway, walking distance to markets, 35 min drive to Boston
Hopkinton
9.2 out of 10, Wonderful, (10 reviews)
"Great place to stay very nice apartment"
United States
Aaron R.
$207 nightly
The price is $231
Sep 1 - Sep 2
Total with taxes and fees
Beautiful family getaway, walking distance to markets, 35 min drive to Boston
1 bedroom, internet, bed sheets

2. Clean & Cozy Private room - 3 floor_R 1

Clean & Cozy Private room - 3 floor_R 1
Union HIll
$100 nightly
The price is $115
Aug 10 - Aug 11
Total with taxes and fees
Clean & Cozy Private room - 3 floor_R 1
Dining

3. Zen Inspired Retreat with Private Forest Trails

Zen Inspired Retreat with Private Forest Trails
Uxbridge
10.0 out of 10, Exceptional, (15 reviews)
"Very comfortable and relaxing on the inside with beautiful surroundings and hiking trails right on the property. Exactly what we wanted for a get-away and such close proximity to the zoo where we attended a wedding."
United States
Tammie K.
$242 nightly
The price is $257
Sep 7 - Sep 8
Total with taxes and fees
Zen Inspired Retreat with Private Forest Trails
Interior

4. Residences at Solomon Pond

Residences at Solomon Pond
3.5 star property
Marlborough
8.2 out of 10, Very Good, (250 reviews)
"Wonderful!!"
United States
Huynh
$129 nightly
The price is $144
Aug 10 - Aug 11
Total with taxes and fees
Residences at Solomon Pond
Private kitchen

5. Charming 3-bedroom house in delightful Ashland for your getaway

Charming 3-bedroom house in delightful Ashland for your getaway
Ashland
10.0 out of 10, Exceptional, (2 reviews)
"This is our second stay here and both times have been good. The house is quiet, even for it being on a well traveled road. "
United States
John W.
$276 nightly
The price is $292
Aug 15 - Aug 16
Total with taxes and fees
Charming 3-bedroom house in delightful Ashland for your getaway
TV

6. Large 3BD 1st Floor Apartment Minutes from 290

Large 3BD 1st Floor Apartment Minutes from 290
Franklin Plantation
10.0 out of 10, Exceptional, (4 reviews)
"It was a great place for my family and i"
United States
Taisha M.
$227 nightly
The price is $260
Aug 11 - Aug 12
Total with taxes and fees
Large 3BD 1st Floor Apartment Minutes from 290
Dining

7. 12B-Cozy 3BR Apartment with Koi Pond in Worcester

12B-Cozy 3BR Apartment with Koi Pond in Worcester
Millbury
9.4 out of 10, Exceptional, (3 reviews)
"Super nice place to stay with lots of food options in the area."
United States
Roberto A G.
$372 nightly
The price is $393
Aug 10 - Aug 11
Total with taxes and fees
12B-Cozy 3BR Apartment with Koi Pond in Worcester
Smart TV, fireplace, books, stereo

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

Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham
Framingham
10.0 out of 10, Exceptional, (6 reviews)
"Very quiet, quaint and so cozy. We’re very satisfied with this property "
United States
roger n.
$191 nightly
The price is $213
Aug 11 - Aug 12
Total with taxes and fees
Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham
3 bedrooms, desk, iron/ironing board, WiFi (free)

9. Clifford Luxury Retreat 3BR Self Check In Home

Clifford Luxury Retreat 3BR Self Check In Home
Northbridge
9.0 out of 10, Wonderful, (2 reviews)
"We loved our stay here. The home and the host were both exceptional. We highly recommend this home!"
United States
Martin G.
$511 nightly
The price is $540
Aug 11 - Aug 12
Total with taxes and fees
Clifford Luxury Retreat 3BR Self Check In Home
TV, fireplace

10. Private Luxury 2 Bedroom Suite

Private Luxury 2 Bedroom Suite
Framingham
8.0 out of 10, Very Good, (11 reviews)
"Homeowner was very warm and welcoming, he accomdated my friend and i for two nights, rooms were very clean, and spacious, provided everything we needed and loved it. Highly recommend."
United States
T U.
$133 nightly
The price is $148
Aug 13 - Aug 14
Total with taxes and fees
Private Luxury 2 Bedroom Suite
Living area

11. Clean & Cozy Private- 3 floor_R 4

Clean & Cozy Private- 3 floor_R 4
Union HIll
$88 nightly
The price is $101
Aug 10 - Aug 11
Total with taxes and fees
Clean & Cozy Private- 3 floor_R 4
3 bedrooms, WiFi

12. Newly Refreshed 3bd Spacious Unit Minutes from 290

Newly Refreshed 3bd Spacious Unit Minutes from 290
Franklin Plantation
9.4 out of 10, Exceptional, (3 reviews)
"The communication was wonderful. There were some things that needed to be addressed and they were.We would definitely rent again! The space is very spacious and clean"
United States
Anonymous traveler
$256 nightly
The price is $293
Aug 12 - Aug 13
Total with taxes and fees
Newly Refreshed 3bd Spacious Unit Minutes from 290
Smart TV

13. Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2

Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
Worcester
10.0 out of 10, Exceptional, (6 reviews)
"Clean, perfect, had everything we needed for a quick stay "
United States
Sierra M.
$339 nightly
The price is $388
Aug 10 - Aug 11
Total with taxes and fees
Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
Interior

14. Angel Sky Challenge

Angel Sky Challenge
Worcester
2.0 out of 10, (1 review)
"The add states an entire home, this is a home with small bedrooms and a bathroom. I was under the impression by the description the entire home was ours without others on the property. I’d put that in the description I felt under comfortable with the men on the property. False advertising "
United States
Cameron R.
$227 nightly
The price is $260
Aug 10 - Aug 11
Total with taxes and fees
Angel Sky Challenge
Smart TV, books

15. Heart of Shrewsbury St – 2BR Stay

Heart of Shrewsbury St – 2BR Stay
Shrewsbury Street
8.0 out of 10, Very Good, (1 review)
"We did not receive information on how to enter the property until we arrived and called the owner. There was a lot of poison ivy growing in our parking area."
United States
Sharon
$241 nightly
The price is $275
Aug 10 - Aug 11
Total with taxes and fees
Heart of Shrewsbury St – 2BR Stay
Living area

16. Clean & Cozy Private-3 floor_R 2

Clean & Cozy Private-3 floor_R 2
Union HIll
$105 nightly
The price is $120
Aug 12 - Aug 13
Total with taxes and fees
Clean & Cozy Private-3 floor_R 2
Interior

17. Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1

Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1
Main South
10.0 out of 10, Exceptional, (1 review)
$307 nightly
The price is $352
Aug 10 - Aug 11
Total with taxes and fees
Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1
Exterior

18. Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (24 reviews)
"I stayed here for the 2026 Natchaug Epic gravel bike ride, and it was an ideal location, close to the start line. A charming property with a friendly host. "
United States
Mateo A.
$166 nightly
The price is $188
Aug 10 - Aug 11
Total with taxes and fees
Wizard's Roost at Underhill Hollow
Living area

19. Clean & Cozy Private- 3 floor_R 3

Clean & Cozy Private- 3 floor_R 3
Union HIll
$106 nightly
The price is $121
Aug 30 - Aug 31
Total with taxes and fees
Clean & Cozy Private- 3 floor_R 3
Living area

20. Clean & Cozy Private- 3 floor_R 5

Clean & Cozy Private- 3 floor_R 5
Union HIll
$106 nightly
The price is $122
Aug 30 - Aug 31
Total with taxes and fees
Clean & Cozy Private- 3 floor_R 5
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Upton Hotel Reviews

Sonesta Select Boston Milford

Sonesta Select Boston Milford

10/10 Excellent
"The Sonesta in Milford Massachusetts was well maintained. The staff was very helpful. I didn’t wake up in time enough to get breakfast, but from what I could tell it was great. The only issue I had was that my door lock wasn’t working, but outside of that the pool was fantastic washing facilities were fantastic. Bathroom was clean. Supplies were refilled. Everything was great. I will be returning."
Jaelyn 2-night trip
Posted less than an hour ago
Sonesta Select Boston Milford

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 $115 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.

Explore a world of travel with Expedia

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 EcoTarium, 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.