Book Holiday Homes in Upton

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Upton

completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore

completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore

Spencer
Located in Spencer, this vacation home is on the waterfront, within a 10-minute drive of Saint Joseph's Abbey and Buck Hill Conservation Dam.
completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.

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

Shrewsbury
Located in Shrewsbury, this vacation home is a 3-minute drive from Ski Ward Ski Area and 5 minutes from New England Baseball Complex.
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
Large relaxing house in 25 acres of private woods with lake access.

Large relaxing house in 25 acres of private woods with lake access.

Spencer
Located in Spencer, this vacation home is on a lake, within a 10-minute drive of Buck Hill Conservation Dam and Moore State Park.
Large relaxing house in 25 acres of private woods with lake access.
Save an average of 15% on thousands of hotels when you're signed in
Cozy home 5 minutes to shopping center, HC college, 2 kitchens, 2 living rooms

Cozy home 5 minutes to shopping center, HC college, 2 kitchens, 2 living rooms

Worcester
Located in Worcester, this vacation home is within a 5-minute drive of Goddard Rocket Launching Site and The Shoppes at Blackstone Valley.
Cozy home 5 minutes to shopping center, HC college, 2 kitchens, 2 living rooms
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

Shrewsbury
Located in Shrewsbury, this vacation home is a 3-minute drive from Ski Ward Ski Area and 5 minutes from New England Baseball Complex.
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
The Tree House at Underhill Hollow

The Tree House at Underhill Hollow

Thompson
The price is AU$290 per night from 26 Nov to 27 Nov
AU$290
includes taxes & fees
26 Nov - 27 Nov
This vacation home is 3.5 mi (5.6 km) from Thompson International Speedway and 4.8 mi (7.8 km) from Bradley Playhouse.
The Tree House at Underhill Hollow
1x1 Serenity in the Suburbs: Your Ideal Retreat in Westborough - Boston

1x1 Serenity in the Suburbs: Your Ideal Retreat in Westborough - Boston

Westborough
The price is AU$263 per night from 21 Dec to 22 Dec
AU$263
includes taxes & fees
21 Dec - 22 Dec
Located in Westborough, this vacation home is within a 10-minute drive of Lake Chauncy Public Beach and Westborough Country Club.
1x1 Serenity in the Suburbs: Your Ideal Retreat in Westborough - Boston
Norwood Luxe Suite-  Pet friendly & Commuter friendly

Norwood Luxe Suite- Pet friendly & Commuter friendly

Norwood
Located in Norwood, this vacation home is within a 10-minute drive of Legacy Place and Blue Hills Reservation.
Norwood Luxe Suite- Pet friendly & Commuter friendly
Cozy bedrooms in Shrewsbury warm town and convenient

Cozy bedrooms in Shrewsbury warm town and convenient

Shrewsbury
Located in Shrewsbury, this vacation home is within a 5-minute drive of Busta Rhymes Island and Quinsigamond State Park.
Cozy bedrooms in Shrewsbury warm town and convenient
Don't see what you're looking for?
See all available properties in Upton
View all properties
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.

Upton Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Upton vacation homes are the perfect way for you to wing it.

Holiday houses in Upton let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Upton in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Upton adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Upton with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Upton vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Upton Holiday Homes essential information

Accommodation
104 Holiday Homes
Lowest Price
AU$143
Highest Price
AU$290
Popular accommodation
completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore, Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku., Large relaxing house in 25 acres of private woods with lake access., Cozy home 5 minutes to shopping center, HC college, 2 kitchens, 2 living rooms, Beautiful 2 Bedrooms with 2 Beds in Shrewsbury , The Tree House at Underhill Hollow, 1x1 Serenity in the Suburbs: Your Ideal Retreat in Westborough - Boston, Norwood Luxe Suite- Pet friendly & Commuter friendly , Cozy bedrooms in Shrewsbury warm town and convenient

Top trending hotels in Upton

Motel 6 Framingham, MA - Boston West

Motel 6 Framingham, MA - Boston West

2 out of 5
1668 Worcester Rd, Framingham, MA
Fully refundable
The price is AU$143 per night from 1 Dec to 2 Dec
AU$143
includes taxes & fees
1 Dec - 2 Dec
Located in Framingham, Motel 6 Framingham, MA - Boston West is within a 5-minute drive of Framingham State University and Framingham Town Common.
Motel 6 Framingham, MA - Boston West
Bally's Twin River Lincoln Casino & Hotel

Bally's Twin River Lincoln Casino & Hotel

3.5 out of 5
100 Twin River Rd, Lincoln, RI
Fully refundableReserve now, pay when you stay
The price is AU$209 per night from 9 Dec to 10 Dec
AU$209
includes taxes & fees
9 Dec - 10 Dec
When you stay at Bally's Twin River Lincoln Casino & Hotel in Lincoln, you'll be in the business district, a 2-minute drive from Twin River Casino and 8 minutes ...
Bally's Twin River Lincoln Casino & Hotel
Courtyard by Marriott Boston Marlborough

Courtyard by Marriott Boston Marlborough

3 out of 5
75 Felton St, Marlborough, MA
Fully refundableReserve now, pay when you stay
The price is AU$218 per night from 26 Nov to 27 Nov
AU$218
includes taxes & fees
26 Nov - 27 Nov
Located in Marlborough, Courtyard by Marriott Boston Marlborough is within a 5-minute drive of Apex Entertainment Center and New England Sports Center.
Courtyard by Marriott Boston Marlborough
Save an average of 15% on thousands of hotels when you're signed in
enVision Hotel & Conference Center Mansfield-Foxboro

enVision Hotel & Conference Center Mansfield-Foxboro

2.5 out of 5
31 Hampshire St, Mansfield, MA
Fully refundableReserve now, pay when you stay
The price is AU$215 per night from 5 Dec to 6 Dec
AU$215
includes taxes & fees
5 Dec - 6 Dec
Located in Mansfield, enVision Hotel & Conference Center Mansfield-Foxboro is in the business district, within a 15-minute drive of Xfinity Center and Hall at ...
enVision Hotel & Conference Center Mansfield-Foxboro
Don't see what you're looking for?
See all available properties in Upton
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.