Book Holiday Homes in Upton

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Featured Holiday Homes in Upton

Newly Renovated Luxury 3-Bed 2-Bath House with Easy Airport Access

Newly Renovated Luxury 3-Bed 2-Bath House with Easy Airport Access

Framingham
The price is AU$423 per night from 12 Nov to 13 Nov
AU$423
12 Nov - 13 Nov
includes taxes & fees
Located in Framingham, this vacation home is within a 5-minute drive of Saxonville Falls and Dam and Athenaeum Hall.
Opens in a new windowNewly Renovated Luxury 3-Bed 2-Bath House with Easy Airport Access
Beautiful Lakefront Home with Private Beach

Beautiful Lakefront Home with Private Beach

Shrewsbury
With a stay at this vacation home in Boylston, you'll be on a lake, within a 15-minute drive of DCU Center and Cyprian Keyes.
Opens in a new windowBeautiful Lakefront Home with Private Beach
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

Shrewsbury
With a stay at this vacation home in Shrewsbury, you'll be within a 15-minute drive of DCU Center and Ski Ward Ski Area.
Opens in a new windowBeautiful 2 Bedrooms with 2 Beds in Shrewsbury
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The Tree House at Underhill Hollow

The Tree House at Underhill Hollow

Thompson
The price is AU$269 per night from 12 Nov to 13 Nov
AU$269
12 Nov - 13 Nov
includes taxes & fees
This vacation home is 3.5 mi (5.6 km) from Thompson International Speedway and 4.8 mi (7.8 km) from Bradley Playhouse.
Opens in a new windowThe Tree House at Underhill Hollow
Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow

North Grosvenordale
The price is AU$245 per night from 23 Nov to 24 Nov
AU$245
23 Nov - 24 Nov
includes taxes & fees
This vacation home is 3.5 mi (5.6 km) from Thompson International Speedway and 4.8 mi (7.8 km) from Bradley Playhouse.
Opens in a new windowWizard's Roost at Underhill Hollow
Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore

Convenient, clean and cozy 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.
Opens in a new windowConvenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore
Waterfront Home with Stunning Views .. Dog friendly , and great fishing !!!

Waterfront Home with Stunning Views .. Dog friendly , and great fishing !!!

Douglas
Located in Douglas, this vacation home is on the waterfront, a 1-minute drive from Manchaug Pond and 6 minutes from Breezy Picnic Grounds & Waterslides.
Opens in a new windowWaterfront Home with Stunning Views .. Dog friendly , and great fishing !!!
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 The Skating Club of Boston and Legacy Place.
Opens in a new windowNorwood Luxe Suite- Pet friendly & Commuter friendly
Spacious 4-bedroom house in charming Worcester with AC, WiFi

Spacious 4-bedroom house in charming Worcester with AC, WiFi

2 out of 5
Worcester
With a stay at this vacation home in Worcester, you'll be within a 5-minute drive of UMass Memorial Medical Center - Hahnemann Campus and Central Rock Climbing ...
Opens in a new windowSpacious 4-bedroom house in charming Worcester with AC, WiFi
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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
120 Holiday Homes
Lowest Price
AU$134
Highest Price
AU$423
Popular accommodation
Newly Renovated Luxury 3-Bed 2-Bath House with Easy Airport Access, Beautiful Lakefront Home with Private Beach, Beautiful 2 Bedrooms with 2 Beds in Shrewsbury , The Tree House at Underhill Hollow, Wizard's Roost at Underhill Hollow, Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore, Waterfront Home with Stunning Views .. Dog friendly , and great fishing !!!, Norwood Luxe Suite- Pet friendly & Commuter friendly , Spacious 4-bedroom house in charming Worcester with AC, WiFi

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 refundableReserve now, pay when you stay
The price is AU$134 per night from 17 Nov to 18 Nov
AU$134
17 Nov - 18 Nov
includes taxes & fees
Located in Framingham, Motel 6 Framingham, MA - Boston West is within a 5-minute drive of Framingham State University and Framingham Town Common.
Opens in a new windowMotel 6 Framingham, MA - Boston West
The Verve Hotel Boston Natick, Tapestry Collection by Hilton

The Verve Hotel Boston Natick, Tapestry Collection by Hilton

3.5 out of 5
1360 Worcester St, Natick, MA
Fully refundableReserve now, pay when you stay
The price is AU$182 per night from 23 Nov to 24 Nov
AU$182
23 Nov - 24 Nov
includes taxes & fees
When you stay at The Verve Hotel Boston Natick, Tapestry Collection by Hilton in Natick, you'll be in the business district, within a 5-minute drive of Natick ...
Opens in a new windowThe Verve Hotel Boston Natick, Tapestry Collection by Hilton
Hampton Inn Boston Natick

Hampton Inn Boston Natick

2.5 out of 5
319 Speen St, Natick, MA
The price is AU$176 per night from 7 Dec to 8 Dec
AU$176
7 Dec - 8 Dec
includes taxes & fees
With a stay at Hampton Inn Boston Natick, you'll be centrally located in Natick, a 6-minute walk from Natick Collection and 11 minutes by foot from Cochituate ...
Opens in a new windowHampton Inn Boston Natick
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Best Western The Inn at Sharon/Foxboro

Best Western The Inn at Sharon/Foxboro

2.5 out of 5
395 Old Post Rd, Sharon, MA
Fully refundableReserve now, pay when you stay
The price is AU$178 per night from 16 Nov to 17 Nov
AU$178
16 Nov - 17 Nov
includes taxes & fees
With a stay at Best Western The Inn at Sharon/Foxboro in Sharon, you'll be in the business district, within a 10-minute drive of Gillette Stadium and Walpole ...
Opens in a new windowBest Western The Inn at Sharon/Foxboro
Don't see what you're looking for?
See all available properties in Upton
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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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^Subject to availability and chosen travel dates.