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Upton Holiday Rentals

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Our top choices for Upton holiday rentals

1. Residences at Solomon Pond

Residences at Solomon Pond
3.5 star property
Marlborough
8.2 out of 10, Very good, (252 reviews)
"Wonderful!!"
United States
Huynh
The price is NZ$189
includes taxes & fees
22 Sept - 23 Sept
Residences at Solomon Pond

2. 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.
The price is NZ$369
includes taxes & fees
24 Sept - 25 Sept
Beautiful family getaway, walking distance to markets, 35 min drive to Boston

3. Clifford Luxury Retreat 3BR Self Check In Home

Clifford Luxury Retreat 3BR Self Check In Home
Northbridge
8.4 out of 10, Very good, (6 reviews)
The price is NZ$929
includes taxes & fees
21 Sept - 22 Sept
Clifford Luxury Retreat 3BR Self Check In Home

4. 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 NZ$445
includes taxes & fees
5 Oct - 6 Oct
Zen Inspired Retreat with Private Forest Trails

5. Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.

Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
Shrewsbury
9.6 out of 10, Exceptional, (37 reviews)
"Lovely and great location "
United States
Kimberlee K.
The price is NZ$496
includes taxes & fees
21 Sept - 22 Sept
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.

6. 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, (6 reviews)
"Super nice place to stay with lots of food options in the area."
United States
Roberto A G.
The price is NZ$816
includes taxes & fees
25 Sept - 26 Sept
12B-Cozy 3BR Apartment with Koi Pond in Worcester

7. Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
Shrewsbury
9.4 out of 10, Exceptional, (54 reviews)
"Amazing host and fabulous spacious property. "
United States
Kelly L.
The price is NZ$516
includes taxes & fees
13 Oct - 14 Oct
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

8. Clean & Cozy Private- 3 floor_R 5

Clean & Cozy Private- 3 floor_R 5
Union HIll
2.0 out of 10, (1 review)
The price is NZ$200
includes taxes & fees
21 Sept - 22 Sept
Clean & Cozy Private- 3 floor_R 5

9. Sakura House: Spacious 4BR w/ Gym & Premium Design

Sakura House: Spacious 4BR w/ Gym & Premium Design
Northborough
10.0 out of 10, Exceptional, (14 reviews)
"Very comfortable stay. Highly recommend it."
United States
Susmitha R.
The price is NZ$1,436
includes taxes & fees
21 Oct - 22 Oct
Sakura House: Spacious 4BR w/ Gym & Premium Design

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

Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access
Framingham
9.6 out of 10, Exceptional, (30 reviews)
"Perfect place to stay. Clean and has everything you need. Would recommend anyone to stay here. "
United States
Michelle M.
The price is NZ$600
includes taxes & fees
22 Sept - 23 Sept
Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access

11. Game Room + Bar Lounge, 35 Min to Boston

Game Room + Bar Lounge, 35 Min to Boston
Worcester
The price is NZ$492
includes taxes & fees
22 Sept - 23 Sept
Game Room + Bar Lounge, 35 Min to Boston

12. Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
9.8 out of 10, Exceptional, (20 reviews)
"Perfect location"
United States
Harmony F.
The price is NZ$884
includes taxes & fees
21 Sept - 22 Sept
Spacious 4-bedroom with four and half bathrooms

13. Spacious 5 Bedroom Retreat • Free Parking • Pet Friendly• Greater Boston

Spacious 5 Bedroom Retreat • Free Parking • Pet Friendly• Greater Boston
Framingham
10.0 out of 10, Exceptional, (5 reviews)
"The house was nice. The beds were very comfortable. The house was close to everything. Check-in and check-out process was easy."
United States
Christina S.
The price is NZ$965
includes taxes & fees
28 Sept - 29 Sept
Spacious 5 Bedroom Retreat • Free Parking • Pet Friendly• Greater Boston

14. 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 NZ$476
includes taxes & fees
24 Sept - 25 Sept
Large 3BD 1st Floor Apartment Minutes from 290

15. 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 NZ$573
includes taxes & fees
21 Sept - 22 Sept
Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2

16. 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 traveller
The price is NZ$466
includes taxes & fees
24 Sept - 25 Sept
Newly Refreshed 3bd Spacious Unit Minutes from 290

17. 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 NZ$417
includes taxes & fees
22 Sept - 23 Sept
Heart of Shrewsbury St – 2BR Stay

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

totally remodeled house with fitness room, close to Boston and Worcester
Framingham
9.4 out of 10, Exceptional, (15 reviews)
"Nicely located in neighbor with easy access to highways and walking distance to coffee shop this single home is perfect for being near Boston. Space is comfortable with all the comforts of home. "
United States
Karyn V.
The price is NZ$560
includes taxes & fees
22 Sept - 23 Sept
totally remodeled house with fitness room, close to Boston and Worcester

19. Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (26 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.
The price is NZ$328
includes taxes & fees
21 Sept - 22 Sept
Wizard's Roost at Underhill Hollow

20. Luxury Boston Ranch –Sleeps 8|Pet+|Heated pool

Luxury Boston Ranch –Sleeps 8|Pet+|Heated pool
Framingham
10.0 out of 10, Exceptional, (6 reviews)
"Very nice"
United States
Tricia S.
The price is NZ$1,184
includes taxes & fees
29 Sept - 30 Sept
Luxury Boston Ranch –Sleeps 8|Pet+|Heated pool
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

Find out more about Upton

Everything you need to know about Upton holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Upton holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Upton holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Upton holiday rentals we have selected for you start as low as NZ$189 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 holiday 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 holiday.

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 holiday rentals in Upton?

Yes, there are holiday rentals close to the most popular sights in Upton, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Upton has to offer?

The Tree House at Underhill Hollow: This holiday home rental outside of Upton offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a coffee maker and kitchenware.

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 wider area, you’ll find Hopkinton State Park and Cummings School of Veterinary Medicine at Tufts University.

What’s a holiday rental in Upton like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Upton. Holiday rentals feature extras such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from public hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for family trips or small group gatherings.