Holiday Homes in Thompson

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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Thompson holiday homes

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 €165
includes taxes & fees
2 Jun - 3 Jun
Wizard's Roost at Underhill Hollow
Interior

Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
10.0 out of 10, Exceptional, (3 reviews)
"I was looking for a place that was central to a couple of Renaissance Faires in the area and ended uo choosing this one due to its location and affordability. What an awesome place to stay. We're considering staying here next year when the Faires return."
United States
Kevan W.
The price is €228
includes taxes & fees
3 Jun - 4 Jun
Spacious, unique barn with beautiful views.
Sailing, kayaking, fishing

Wonderful Suite In a Charming Bed and Breakfast for a Weekend Getaway near Shenipsit State Forest, Connecticut

Wonderful Suite In a Charming Bed and Breakfast for a Weekend Getaway near Shenipsit State Forest, Connecticut
Stafford Springs
The price is €204
includes taxes & fees
2 Jun - 3 Jun
Wonderful Suite In a Charming Bed and Breakfast for a Weekend Getaway near Shenipsit State Forest, Connecticut
Interior

The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (37 reviews)
"Such a fun getaway!"
United States
Patrice D.
The price is €170
includes taxes & fees
2 Jun - 3 Jun
The Tree House at Underhill Hollow
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 €165
includes taxes & fees
2 Jun - 3 Jun
SteamPunk Bunk House and Intergalactic Way Station
Dining

Lovely Historic Vintage home. Remodeled inside.

Lovely Historic Vintage home. Remodeled inside.
Johnston
9.2 out of 10, Wonderful, (41 reviews)
"My host was awesome. The house was is a nice neighborhood everything we needs so close. "
United States
Tina N.
The price is €354
includes taxes & fees
9 Jun - 10 Jun
Lovely Historic Vintage home. Remodeled inside.
Outdoor dining

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Ashford
9.6 out of 10, Exceptional, (21 reviews)
"The location of the home was perfect. The lake was beautiful and was a great place to walk. "
United States
Lynn D.
The price is €240
includes taxes & fees
2 Jun - 3 Jun
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Exterior

Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
The price is €165
includes taxes & fees
2 Jun - 3 Jun
Cottage by the Castle – Downtown Spencer
Dining

Beautiful Worcester Downtown King Bd/Office World Cup Boston

Beautiful Worcester Downtown King Bd/Office World Cup Boston
Worcester
10.0 out of 10, Exceptional, (1 review)
"I had an amazing stay here and would absolutely recommend this place to anyone visiting Boston or Worcester, Massachusetts. The house was truly 100% excellent. Everything was incredibly clean, spacious, and well organized. I loved the kitchen, my room, and the bathroom, everything was spotless and very comfortable. Honestly, the entire home was sparkling clean and very welcoming.I also slept extremely well during my stay. The bed, pillows, and bedding were so comfortable, which made the...
United States
Masard T.
The price is €359
includes taxes & fees
7 Jun - 8 Jun
Beautiful Worcester Downtown King Bd/Office World Cup Boston
Property grounds

Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8

Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Brimfield
8.8 out of 10, Excellent, (3 reviews)
"Excellent communicative host with warm welcome and delightful amenities. Quiet neighborhood with plenty of parking."
United States
Pamela L.
The price is €217
includes taxes & fees
29 Jun - 30 Jun
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
TV

6 Beds Home w/Game Room Perfect for Groups

6 Beds Home w/Game Room Perfect for Groups
Killingly
6 Beds Home w/Game Room Perfect for Groups
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, (12 reviews)
"10/10 great place to stay"
United States
Tyler B.
The price is €434
includes taxes & fees
2 Jun - 3 Jun
Spacious 4-bedroom with four and half bathrooms
Property grounds

Family-friendly 2- Bedroom Webster Home w/Cozy Balcony

Family-friendly 2- Bedroom Webster Home w/Cozy Balcony
Webster
9.6 out of 10, Exceptional, (5 reviews)
"Owner was easy to communicate with. Cute and cozy unit that meet all of our needs for our trip."
United States
Rachele T.
The price is €320
includes taxes & fees
9 Jun - 10 Jun
Family-friendly 2- Bedroom Webster Home w/Cozy Balcony
Terrace/patio

Stunning Lakefront Escape! Book Your Dream Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!
Woodstock
10.0 out of 10, Exceptional, (25 reviews)
"Welcoming host! Beautiful house with great amenities!"
United States
maria c.
The price is €640
includes taxes & fees
2 Jun - 3 Jun
Stunning Lakefront Escape! Book Your Dream Getaway!
Dining

Clifford Luxury Retreat 3BR Self Check In Home

Clifford Luxury Retreat 3BR Self Check In Home
Northbridge
The price is €415
includes taxes & fees
3 Jun - 4 Jun
Clifford Luxury Retreat 3BR Self Check In Home
TV, fireplace

Sleeps 15 • Pool • World Cup 2026 • Retreat

Sleeps 15 • Pool • World Cup 2026 • Retreat
Brimfield
10.0 out of 10, Exceptional, (34 reviews)
"We visited in December, so the pool was closed, but looked inviting even in the snow. The home was so warm and cozy and spacious. We loved our stay."
United States
Gina O.
The price is €1,508
includes taxes & fees
3 Jun - 4 Jun
Sleeps 15 • Pool • World Cup 2026 • Retreat
Dining

Secluded 2-Acre Lakefront Home! Book Your Getaway!

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (84 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
The price is €666
includes taxes & fees
2 Jun - 3 Jun
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Interior

Cozy 3-bedroom house in serene Worcester with fitness room and office

Cozy 3-bedroom house in serene Worcester with fitness room and office
Worcester
The price is €398
includes taxes & fees
2 Jun - 3 Jun
Cozy 3-bedroom house in serene Worcester with fitness room and office
Interior

Lake House in Sturbridge w/All the Views!

Lake House in Sturbridge w/All the Views!
Sturbridge
9.6 out of 10, Exceptional, (21 reviews)
"Thank you for a wonderful stay! Our family enjoyed the gorgeous views and the well-equipped home. There were toys, books, and games for the kids, and the beds were very comfortable. We’d definitely stay again!"
United States
Caitlin D.
The price is €745
includes taxes & fees
2 Jun - 3 Jun
Lake House in Sturbridge w/All the Views!
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 Thompson Hotel Reviews

Holiday Inn Express Boston - Milford by IHG

Holiday Inn Express Boston - Milford by IHG

10/10 Excellent
"Even during their renovations, the hotel is well maintained cleanliness is exceptional. Breakfast is amazing. Also, the front desk is super helpful especially a gentleman by the name of Chaz has been nothing but over the top exceptional customer service and beyond I give this a five star rating."
scotty 9-night trip
Posted 4 hours ago
Holiday Inn Express Boston - Milford by IHG

Find out more about Thompson

Thompson Holiday Homes information

Number of reviews
282
Accommodation
105 Holiday Homes
Lowest Price
€165
Highest Price
€1,508