Upton Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Upton vacation rentals

A dining area with a round table, yellow chairs, a potted plant, and a Buddha painting on the wall.

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
9.4 out of 10, Exceptional, (11 reviews)
"Great place to stay very nice apartment"
United States
Aaron R.
The price is CA $224
CA $312 total
includes taxes & fees
Dec 2 - Dec 3
Beautiful family getaway, walking distance to markets, 35 min drive to Boston
A spacious room with large windows, a wooden dining table with chairs, and a view of the outdoors.

2. Zen Inspired Retreat with Private Forest Trails

Zen Inspired Retreat with Private Forest Trails
Uxbridge
10.0 out of 10, Exceptional, (16 reviews)
"This was a lovely place to stay! This site was meticulously clean, gardens and decor both zen and whimsical, trails well maintained, near a grocery and other shopping. I will stay again!"
United States
Melanie S.
The price is CA $304
CA $352 total
includes taxes & fees
Dec 7 - Dec 8
Zen Inspired Retreat with Private Forest Trails
A living room with a TV, sofa, chairs, a lamp, and a window with sheer curtains.

3. Clean & Cozy Private-3 floor_R 2

Clean & Cozy Private-3 floor_R 2
Union HIll
9.0 out of 10, Wonderful, (2 reviews)
"Nice and very clean. Host communicated fast and helpful."
United States
Ekaterina
The price is CA $113
CA $149 total
includes taxes & fees
Nov 17 - Nov 18
Clean & Cozy Private-3 floor_R 2
A modern hotel lobby with a seating area, a bar, and a kitchen.

4. Residences at Solomon Pond

Residences at Solomon Pond
3.5 star property
Marlborough
8.2 out of 10, Very good, (268 reviews)
"Friendly front desk. Clean and pleasant room. Would stay again."
United States
Tae
The price is CA $154
CA $172 total
includes taxes & fees
Nov 12 - Nov 13
Residences at Solomon Pond
A living room with a gray sofa, a coffee table, and a rug. There are two windows with blinds, a door, and a wall-mounted plant.

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

Large 3BD 1st Floor Apartment Minutes from 290
Franklin Plantation
10.0 out of 10, Exceptional, (5 reviews)
"It was a great place for my family and i"
United States
Taisha M.
The price is CA $224
CA $443 total
includes taxes & fees
Nov 12 - Nov 13
Large 3BD 1st Floor Apartment Minutes from 290
A cozy attic bedroom with a skylight, a piano, a mirror, and a bedside table with a lamp.

6. Clifford Luxury Retreat 3BR Self Check In Home

Clifford Luxury Retreat 3BR Self Check In Home
Northbridge
8.6 out of 10, Excellent, (7 reviews)
"We loved our stay here. The home and the host were both exceptional. We highly recommend this home!"
United States
Martin G.
The price is CA $546
CA $598 total
includes taxes & fees
Nov 13 - Nov 14
Clifford Luxury Retreat 3BR Self Check In Home
A living room with a TV, a sofa, a chair, a lamp, and a window with sheer curtains.

7. Clean & Cozy Private room - 3 floor_R 1

Clean & Cozy Private room - 3 floor_R 1
Union HIll
4.0 out of 10, (3 reviews)
The price is CA $126
CA $163 total
includes taxes & fees
Nov 13 - Nov 14
Clean & Cozy Private room - 3 floor_R 1
A modern living room with a flat-screen TV, a sofa, and two armchairs. There is a dining area with a kitchen in the background.

8. 12B-Cozy 3BR Apartment with Koi Pond in Worcester

12B-Cozy 3BR Apartment with Koi Pond in Worcester
Millbury
9.8 out of 10, Exceptional, (7 reviews)
"Super nice place to stay with lots of food options in the area."
United States
Roberto A G.
The price is CA $220
CA $493 total
includes taxes & fees
Nov 12 - Nov 13
12B-Cozy 3BR Apartment with Koi Pond in Worcester
Living area

9. 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.
The price is CA $166
CA $467 total
includes taxes & fees
Nov 12 - Nov 13
Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
A living room with a sofa, a coffee table, a TV, and a hallway leading to other rooms.

10. Private Luxury 2 Bedroom Suite

Private Luxury 2 Bedroom Suite
Framingham
8.2 out of 10, Very good, (14 reviews)
"Overall we had a great time"
United States
David W.
The price is CA $174
CA $214 total
includes taxes & fees
Nov 17 - Nov 18
Private Luxury 2 Bedroom Suite
A living room with a TV, sofa, chairs, a lamp, and a window with sheer curtains.

11. Clean & Cozy Private- 3 floor_R 4

Clean & Cozy Private- 3 floor_R 4
Union HIll
4.0 out of 10, (1 review)
"Expedia described this as a 3rd floor 1 bedroom apartment. Had I known it was basically a boarding house/hostel, I wouldn’t have booked. Also 1 dingy towel offered for showering. No utensils, no hair dryer (even though it was listed) so what good is a stovetop and pans with zero utensils, including no forks/spoons, spatulas etc."
United States
Martina
The price is CA $97
CA $130 total
includes taxes & fees
Nov 17 - Nov 18
Clean & Cozy Private- 3 floor_R 4
A living room with a grey sofa, two armchairs, a coffee table, and a large painting on the wall.

12. 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, (11 reviews)
"Very quiet, quaint and so cozy. We’re very satisfied with this property "
United States
roger n.
The price is CA $186
CA $304 total
includes taxes & fees
Dec 1 - Dec 2
Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham
A living room with a TV, sofa, chairs, a lamp, and a window with sheer curtains.

13. Clean & Cozy Private- 3 floor_R 3

Clean & Cozy Private- 3 floor_R 3
Union HIll
The price is CA $126
CA $163 total
includes taxes & fees
Nov 13 - Nov 14
Clean & Cozy Private- 3 floor_R 3
A modern kitchen with stainless steel appliances, wooden ceiling, and a dining area with a wooden table and chairs.

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

Charming single family Cottage, pet friendly, close to Prov, Woon, MA & highways
Lincoln
10.0 out of 10, Exceptional, (34 reviews)
"Everything was clean and welcoming. Kitchen had everything you need to cook, make coffee, etc. charming and comfortable "
United States
Lindsey D.
The price is CA $172
CA $301 total
includes taxes & fees
Nov 30 - Dec 1
Charming single family Cottage, pet friendly, close to Prov, Woon, MA & highways
A spacious living room with a high ceiling, a wooden floor, a black sofa, a white armchair, a small round table, and a window with curtains.

15. Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston

Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston
Worcester
8.0 out of 10, Very good, (1 review)
"The house was fine overall. There were just a few things that stood out - only 3 towels but we were 4, no baking sheet for the oven, lighting in the kitchen wasn’t great, couldn’t find the house or unit number and the lock box was hard to find. The main bed was very comfortable but the pillows were not."
United States
Laura P.
The price is CA $361
CA $445 total
includes taxes & fees
Nov 12 - Nov 13
Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston
A living room with two sofas, a coffee table, and a bookshelf.

16. 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
The price is CA $259
CA $321 total
includes taxes & fees
Nov 17 - Nov 18
Heart of Shrewsbury St – 2BR Stay
A room with two black leather sofas, a glass-top coffee table, white walls, and a ceiling light.

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
8.8 out of 10, Excellent, (3 reviews)
"Rented the property to attend a series of events at Clark University. Literally walking distance to the school so it was quite convenient. Apartment was clean, beds were comfortable. Being able to park three cars in the driveway was a huge plus as street parking near the apartment was extremely challenging. Being a Clark alum, was quite familiar with the neighborhood so I knew what to expect. Felt completely safe in the apartment as every door to the hallways had sufficient locks. We did blow a...
United States
Elyse D.
The price is CA $210
CA $487 total
includes taxes & fees
Dec 1 - Dec 2
Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1
A two-story house with a central entrance, a brick foundation, and a large front yard.

18. 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.
The price is CA $226
CA $352 total
includes taxes & fees
Nov 13 - Nov 14
Angel Sky Challenge
A red building with a colorful mural on the front, a covered porch, and a stone foundation.

19. Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (26 reviews)
"Great stay!!"
United States
Elizabeth G.
The price is CA $178
CA $255 total
includes taxes & fees
Nov 12 - Nov 13
Wizard's Roost at Underhill Hollow
A room with a sloped ceiling, wooden beams, a purple door, and a star decoration on the wall.

20. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (46 reviews)
"Nice place to stay has good air conditioning "
United States
Zachary P.
The price is CA $178
CA $262 total
includes taxes & fees
Nov 12 - Nov 13
The Tree House at Underhill Hollow
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

A Holiday Inn Express hotel with a covered entrance and a clear sky.
Holiday Inn Express Boston - Milford by IHG

Holiday Inn Express Boston - Milford by IHG

Holiday Inn Express Boston - Milford by IHG
Milford

10/10 Excellent

Clean and quiet.
Canada
Andrew
Reviewed October 27, 2026
Holiday Inn Express Boston - Milford by IHG

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, cottages, cabins, villas... 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Upton vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Upton vacation rentals we have selected for you start as low as CA $113 per night. Entering your travel dates in the search wizard 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.

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?

Totally remodeled house with fitness room, close to Boston and Worcester : Located near Upton, this vacation home rental is equipped with a patio, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

What’s there to see and do in Upton?

While exploring the area, visit family-friendly sights like Apex Entertainment Center, 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.