Upton Holiday Rentals

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Check prices for these dates

In two weeks
8 May - 10 May
In two months
19 Jun - 21 Jun
In three months
17 Jul - 19 Jul
In four months
14 Aug - 16 Aug

Our top choices for Upton holiday rentals

Fridge, microwave, oven, stovetop

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, (24 reviews)
"Everything was fine, place is clean and convenient"
United States
Tyson P.
The price is HK$769
HK$1,502 total
includes taxes & fees
17 May - 18 May
Charming single family Cottage, pet friendly, close to Prov, Woon, MA & highways
Smart TV, fireplace

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, (4 reviews)
"Very nice and private. Reasonably close to commuter lines into Boston."
United States
Jenny S.
The price is HK$1,019
HK$1,672 total
includes taxes & fees
28 Apr - 29 Apr
Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham
Property grounds

SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (14 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is HK$987
HK$1,472 total
includes taxes & fees
27 Apr - 28 Apr
SteamPunk Bunk House and Intergalactic Way Station
Interior

The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.2 out of 10, Wonderful, (35 reviews)
"Such a fun getaway!"
United States
Patrice D.
The price is HK$987
HK$1,517 total
includes taxes & fees
27 Apr - 28 Apr
The Tree House at Underhill Hollow
Exterior

Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (22 reviews)
"Full of whimsy, loved all of the details of the construction and decor. Great place to stay"
United States
Meghann H.
The price is HK$987
HK$1,472 total
includes taxes & fees
27 Apr - 28 Apr
Wizard's Roost at Underhill Hollow
Living area

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

Welcome in this charming one bedroom apartment located in Westwood. WorldCup2026
Westwood
The price is HK$987
HK$1,505 total
includes taxes & fees
19 May - 20 May
Welcome in this charming one bedroom apartment located in Westwood. WorldCup2026
Fridge, microwave, stovetop, coffee/tea maker

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

totally remodeled house with fitness room, close to Boston and Worcester
Framingham
9.0 out of 10, Wonderful, (10 reviews)
"Property was as described. It was clean and owner was very responsive. Could walk to great coffee shop. "
United States
michelle s.
The price is HK$1,262
HK$2,364 total
includes taxes & fees
27 Apr - 28 Apr
totally remodeled house with fitness room, close to Boston and Worcester
1 bedroom, iron/ironing board, WiFi, bed sheets

The Studio-Suite at Putnam Pike NEW APT Near PVD

The Studio-Suite at Putnam Pike NEW APT Near PVD
Johnston
The price is HK$1,481
HK$2,680 total
includes taxes & fees
28 Apr - 29 Apr
The Studio-Suite at Putnam Pike NEW APT Near PVD
TV, fireplace

Private Luxury 2 Bedroom Suite

Private Luxury 2 Bedroom Suite
Framingham
8.0 out of 10, Very good, (2 reviews)
"Good stay! Host was extremely nice and welcoming! It snowed during the night of the stay, and they were nice enough to still shovel a path in the morning and even cleared a path around my vehicle. Thank you! There is only a microwave, but easy to make work for food options. "
United States
Logan R.
The price is HK$882
HK$1,160 total
includes taxes & fees
27 Apr - 28 Apr
Private Luxury 2 Bedroom Suite
Dining

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 HK$1,121
HK$1,646 total
includes taxes & fees
27 Apr - 28 Apr
Beautiful family getaway, walking distance to markets, 35 min drive to Boston
Dining

Beautiful Worcester Downtown King Bd/Office World Cup Boston

Beautiful Worcester Downtown King Bd/Office World Cup Boston
Worcester
The price is HK$917
HK$2,332 total
includes taxes & fees
27 Apr - 28 Apr
Beautiful Worcester Downtown King Bd/Office World Cup Boston
Smart TV, fireplace

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
9.8 out of 10, Exceptional, (19 reviews)
"Clean home, comfortable beds, host very responsive."
United States
Richard M.
The price is HK$1,678
HK$2,391 total
includes taxes & fees
4 May - 5 May
Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access
Front of property

Lakefront Cottage 2 Mi to Palladium in Worcester!

Lakefront Cottage 2 Mi to Palladium in Worcester!
3.0 star property
Worcester
The price is HK$1,418
HK$3,406 total
includes taxes & fees
19 May - 20 May
Lakefront Cottage 2 Mi to Palladium in Worcester!
Dining

Zen Inspired Retreat with Private Forest Trails

Zen Inspired Retreat with Private Forest Trails
Uxbridge
10.0 out of 10, Exceptional, (14 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.
The price is HK$1,681
HK$2,020 total
includes taxes & fees
27 Apr - 28 Apr
Zen Inspired Retreat with Private Forest Trails
Living area

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

Charming 1-bedroom apartment with AC, WiFi in pleasant Webster
Webster
10.0 out of 10, Exceptional, (1 review)
"Perfect quiet place to work and rest"
United States
michael C.
The price is HK$1,410
HK$3,256 total
includes taxes & fees
27 Apr - 28 Apr
Charming 1-bedroom apartment with AC, WiFi in pleasant Webster
4 bedrooms, iron/ironing board, free WiFi, bed sheets

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

Spacious 4BR Family Home in Worcester near Parks 16/2
Worcester
10.0 out of 10, Exceptional, (3 reviews)
"Clean, perfect, had everything we needed for a quick stay "
United States
Sierra M.
The price is HK$1,199
HK$2,941 total
includes taxes & fees
27 Apr - 28 Apr
Spacious 4BR Family Home in Worcester near Parks 16/2
Fridge, microwave, oven, stovetop

Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
10.0 out of 10, Exceptional, (10 reviews)
"We needed a place to stay while our hardwood floors were being refinished and this was perfect. We have a dog and 2 cats and there was plenty of space. The house was clean and as advertised."
United States
Deb H.
The price is HK$2,155
HK$4,000 total
includes taxes & fees
27 Apr - 28 Apr
Spacious 4-bedroom with four and half bathrooms
Terrace/patio

Lovely & Spacious 2 Br, W/King/Queen beds 2 Bath.

Lovely & Spacious 2 Br, W/King/Queen beds 2 Bath.
Shrewsbury
9.2 out of 10, Wonderful, (17 reviews)
"Great pet friendly, comfy place to stay. The host was extremely helpful."
United States
Kelly L.
The price is HK$1,551
HK$2,827 total
includes taxes & fees
18 May - 19 May
Lovely & Spacious 2 Br, W/King/Queen beds 2 Bath.
Smart TV, books

Heart of Shrewsbury St – 2BR Stay

Heart of Shrewsbury St – 2BR Stay
Shrewsbury Street
The price is HK$1,657
HK$2,121 total
includes taxes & fees
27 Apr - 28 Apr
Heart of Shrewsbury St – 2BR Stay
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

DoubleTree by Hilton Hotel Boston - Westborough

DoubleTree by Hilton Hotel Boston - Westborough

10/10 Excellent
"Did what it needed to do for a one night stay."
Jeremy 1-night trip
Posted 5 hours ago
DoubleTree by Hilton Hotel Boston - Westborough

Find out more about Upton

Search for holiday rentals in Upton on Expedia! You can easily find your home rentals, villas, holiday apartments in Upton using one of the methods below:

  • View our selection of featured holiday rentals in Upton
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Look no further and take a look at our great range of rental properties in Upton!

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?

Home Away from Home!: This holiday home rental outside of 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and 1 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 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.