Holiday Rentals Upton from £75: Find Short-Term Rentals & Holiday Accommodations

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Upton holiday 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

Hopkinton

Aaron R.

includes taxes & fees

4 Oct - 5 Oct

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

Uxbridge

Melanie S.

includes taxes & fees

5 Oct - 6 Oct

A cozy attic bedroom with a skylight, a piano, a mirror, and a bedside table with a lamp.

3. Clifford Luxury Retreat 3BR Self Check In Home

Northbridge

includes taxes & fees

5 Oct - 6 Oct

A modern hotel lobby with a seating area, a bar, and a kitchen.

4. Residences at Solomon Pond

Marlborough

Huynh

includes taxes & fees

2 Nov - 3 Nov

A kitchen with wooden cabinets, a window with a view, a vase with flowers, and framed pictures on the windowsill.

5. 12B-Cozy 3BR Apartment with Koi Pond in Worcester

Millbury

Roberto A G.

includes taxes & fees

7 Oct - 8 Oct

A living room with a sofa, a clock, a floor lamp, and a rug.

6. Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

Shrewsbury

Kelly L.

includes taxes & fees

14 Oct - 15 Oct

A bedroom with a large bed, a desk, a chair, a mirror, and a clock on the wall.

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

Worcester

includes taxes & fees

4 Oct - 5 Oct

8. Breezy 4BR Worcester Home • Pet-Friendly • Summer Fun near I-290 & Parks 16-3

Worcester

Andrew O.

includes taxes & fees

4 Oct - 5 Oct

A living room with two sofas, a coffee table, and a bookshelf.

9. Heart of Shrewsbury St – 2BR Stay

Shrewsbury Street

Sharon

includes taxes & fees

6 Oct - 7 Oct

A living room with a TV, sofa, chairs, a lamp, and a window with sheer curtains.

10. Clean & Cozy Private-3 floor_R 2

Union HIll

includes taxes & fees

5 Oct - 6 Oct

A modern kitchen with a stainless steel refrigerator, double sink, and wooden flooring.

11. Spacious 4-bedroom with four and half bathrooms

Worcester

Harmony F.

includes taxes & fees

4 Oct - 5 Oct

A living room with a sofa, a coffee table, a TV, and a hallway leading to other rooms.

12. Private Luxury 2 Bedroom Suite

Framingham

Beth H.

includes taxes & fees

20 Oct - 21 Oct

A modern kitchen with white cabinetry, a built-in oven, and a dining area with a table and chairs.

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

Framingham

Michelle M.

includes taxes & fees

5 Oct - 6 Oct

A red building with a colorful mural on the front, a covered porch, and a stone foundation.

14. Wizard's Roost at Underhill Hollow

North Grosvenordale

Mateo A.

includes taxes & fees

4 Oct - 5 Oct

A room with two black leather sofas, a glass-top coffee table, white walls, and a ceiling light.

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

Main South

"The host was very communicative and obviously has tried to make this unit a reasonable place to have people stay. However, the layout of the place was not ideal. They turned a front sitting room into a bedroom, but it doesn't really work well. Further, that room smelled like marijuana our whole stay (1-night). It connected to the stairwell up to the units above, and my guess is that those people just smoke weed all day/night and it's impacting this unit. Further, the outside of the house is...

Jeffrey B.

includes taxes & fees

4 Oct - 5 Oct

A living room with a grey sofa, two armchairs, a coffee table, and a large painting on the wall.

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

Framingham

roger n.

includes taxes & fees

27 Oct - 28 Oct

A compact, modern laundry room with a built-in washer and dryer, a small storage cabinet, and a tiled floor.

17. Angel Sky Challenge

Worcester

Cameron R.

includes taxes & fees

4 Oct - 5 Oct

A modern kitchen with white cabinets, a central island, a microwave, and a stove.

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

Framingham

Karyn V.

includes taxes & fees

2 Nov - 3 Nov

A modern living room with a blue sofa, a leather armchair, and a patterned rug.

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

Framingham

Tricia S.

includes taxes & fees

8 Oct - 9 Oct

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

Thompson

Douglas C.

includes taxes & fees

5 Oct - 6 Oct

View all properties

Find holiday rentals that suit your style

Apartments

Private holiday homes

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Upton Hotel Reviews

Hampton Inn Boston Natick

10/10 Excellent

"Wonderful stay!"

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, apart-hotels, 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 £75 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?

Totally remodeled house with fitness room, close to Boston and Worcester : This holiday home rental outside of Upton 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 that 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 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.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Upton holiday rentals

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

2. Zen Inspired Retreat with Private Forest Trails