Upton Holiday Rentals

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Holiday Rentals in Upton

Residences at Solomon Pond

3.5 star property
8.2 out of 10, Very good, (189)
"I really enjoy staying here, the staff is amazingly polite and will try and do their best to make your experience exceptional. "
Residences at Solomon Pond

The Tree House at Underhill Hollow

9.2 out of 10, Wonderful, (25)
"Great stay and the tree house was amazing. We loved walking the trails and finding all the fairy houses and interacting with the animals! "
The price is AU$267
includes taxes & fees
17 Aug - 18 Aug
The Tree House at Underhill Hollow

Wizard's Roost at Underhill Hollow

9.4 out of 10, Exceptional, (14)
"My kids loved all the "magic"(even the grumpy teenager thought it was cool) loved meeting the goats/sheep. We especially loved meeting the farm dog!"
The price is AU$243
includes taxes & fees
25 Aug - 26 Aug
Wizard's Roost at Underhill Hollow

Beautiful Lakefront Home with Private Beach

9.2 out of 10, Wonderful, (173)
"Beautiful house and grounds! Very private with lots of room along with homey touches. Kids loved the toy cabinet and the pool table. Easy access to Boston. We thoroughly enjoyed our Easter weekend there! "
Beautiful Lakefront Home with Private Beach

Spacious 4-bedroom with four and half bathrooms

10.0 out of 10, Exceptional, (1)
"We had room for each of the adults, which included adult children. At these ages they no longer want to share a bed or bathroom with anyone. Perfect that we could come together, but have our own separate spaces. Very clean and comfortable with everything you need."
The price is AU$799
includes taxes & fees
20 Aug - 21 Aug
Spacious 4-bedroom with four and half bathrooms

Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore

10.0 out of 10, Exceptional, (191)
"This was our third time staying, and definately won’t be our last!"
Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore

Charming single family Cottage w fenced in yard, pet friendly, fenced yard

2.0 star property
10.0 out of 10, Exceptional, (14)
"Beautiful little getaway! Pet friendly and very accommodating. Thank you!"
The price is AU$304
includes taxes & fees
12 Sept - 13 Sept
Charming single family Cottage w fenced in yard, pet friendly, fenced yard

Charming 4-bedroom house with WiFi, AC in amazing Foxborough

10.0 out of 10, Exceptional, (11)
"The house is gorgeous and huge! Great place for our adult children and us to hang while attending concert at Gillette. "
The price is AU$1,680
includes taxes & fees
19 Aug - 20 Aug
Charming 4-bedroom house with WiFi, AC in amazing Foxborough

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

9.6 out of 10, Exceptional, (23)
"In town for wedding, great stay for the boylston area!"
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.

Home Near Skiing & Downtown Worcester

3.0 star property
Home Near Skiing & Downtown Worcester

Spacious Private Entrance Master Bedroom/Bath

10.0 out of 10, Exceptional, (86)
"Great place to stay. "
The price is AU$238
includes taxes & fees
28 Aug - 29 Aug
Spacious Private Entrance Master Bedroom/Bath

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

9.8 out of 10, Exceptional, (7)
"This house was just what our family needed for a “home base” while we enjoyed a few days in central New England. It was comfortable and clean, and it was easy to prepare meals when we ate in or packed lunches. Lin was very quick and helpful with communication, and I’d definitely stay again when we’re next In the area!"
The price is AU$460
includes taxes & fees
20 Aug - 21 Aug
Newly Renovated Luxury 3-Bed 2-Bath House with Easy Airport Access

Leicester Lake Front Home, Come Relax!

10.0 out of 10, Exceptional, (26)
"Great family time and comfortable house to spend time with family during a visit to see our daughter at Holy Cross! "
Leicester Lake Front Home, Come Relax!

SteamPunk Bunk House and Intergalactic Way Station

10.0 out of 10, Exceptional, (8)
"This was a charming little apartment with a unique steam punk alien theme. If you have a playful mindset, I highly recommend staying at this location. I couldn’t have been more overjoyed with my stay."
The price is AU$258
includes taxes & fees
25 Aug - 26 Aug
SteamPunk Bunk House and Intergalactic Way Station

Gorgeous, Peaceful Sanctuary on lake minutes from Boston & all local colleges.

10.0 out of 10, Exceptional, (4)
"The home is beautiful, the owner is fantastic and easy to communicate with, check in was easy, comfortable beds, they provide daily cleaning as needed and home was in a great safe area with easy access to Boston."
Gorgeous, Peaceful Sanctuary on lake minutes from Boston & all local colleges.

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

2.0 star property
10.0 out of 10, Exceptional, (16)
"Our stay at this property was great. Very clean and spacious. Area was very accessible to main roads. Our hosts were very responsive from booking through to the end of our stay. Will look to stay next time we visit Worcester "
Spacious 4-bedroom house in charming Worcester with AC, WiFi

Worcester Home on Indian Lake w/ Shared Boat Dock!

3.0 star property
8.0 out of 10, Very good, (1)
Worcester Home on Indian Lake w/ Shared Boat Dock!

Home Away from Home!

9.2 out of 10, Wonderful, (11)
"Lots of bedrooms with a great family gathering space. Quiet neighborhood. Would stay again at this property. Nicely decorated. "
The price is AU$614
includes taxes & fees
17 Aug - 18 Aug
Home Away from Home!

A 125 year old lake property & you won’t believe it! Great fishing spot!

9.8 out of 10, Exceptional, (18)
"The h9mw, grounds and lake were perfect for all ages to enjoy visiting and playing together."
A 125 year old lake property & you won’t believe it! Great fishing spot!

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

10.0 out of 10, Exceptional, (128)
"Wonderful location!!!"
Waterfront Home with Stunning Views .. Dog friendly , and great fishing !!!
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

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?

The Tree House at Underhill Hollow: This holiday home rental outside of Upton offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a coffee maker and kitchenware.

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.