Book Holiday Homes in Upton

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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 within a 15-minute drive of Union Station and DCU Center.
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.
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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
With a stay at this vacation home in Worcester, you'll be within a 10-minute drive of Union Station and DCU Center.
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
With a stay at this vacation home in Shrewsbury, you'll be within a 15-minute drive of Union Station and DCU Center.
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$287 per night from 6 Nov to 7 Nov
AU$287
includes taxes & fees
6 Nov - 7 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$260 per night from 6 Nov to 7 Nov
AU$260
includes taxes & fees
6 Nov - 7 Nov
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
With a stay at this vacation home in Shrewsbury, you'll be within a 10-minute drive of Union Station and DCU Center.
Cozy bedrooms in Shrewsbury warm town and convenient
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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
104 Holiday Homes
Lowest Price
AU$152
Highest Price
AU$287
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$155 per night from 7 Nov to 8 Nov
AU$155
includes taxes & fees
7 Nov - 8 Nov
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
Red Roof Inn Boston - Southborough/ Worcester

Red Roof Inn Boston - Southborough/ Worcester

2 out of 5
367 Turnpike Rd, Southborough, MA
Fully refundableReserve now, pay when you stay
The price is AU$152 per night from 1 Dec to 2 Dec
AU$152
includes taxes & fees
1 Dec - 2 Dec
A stay at Red Roof Inn Boston - Southborough/ Worcester places you in the heart of Southborough, a 4-minute drive from Lake Chauncy Public Beach and 5 minutes ...
Red Roof Inn Boston - Southborough/ Worcester
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$206 per night from 19 Nov to 20 Nov
AU$206
includes taxes & fees
19 Nov - 20 Nov
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 9 minutes ...
Bally's Twin River Lincoln Casino & Hotel
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Red Roof Inn PLUS+ Boston - Framingham

Red Roof Inn PLUS+ Boston - Framingham

2.5 out of 5
650 Cochituate Rd, Framingham, MA
Fully refundableReserve now, pay when you stay
The price is AU$164 per night from 3 Dec to 4 Dec
AU$164
includes taxes & fees
3 Dec - 4 Dec
Located in Framingham, Red Roof Inn PLUS+ Boston - Framingham is in the business district, within a 15-minute walk of Cochituate State Park and Natick ...
Red Roof Inn PLUS+ Boston - Framingham
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.