A snow-covered rural road with a red barn and leafless trees.

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Check prices for these dates

In two weeks
11 Sep - 13 Sep
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Charlton vacation homes

Interior

1. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (41 reviews)
"Great space, lots of fun."
United States
Douglas C.
The price is AED 463
AED 715 total
includes taxes & fees
31 Aug - 1 Sep
The Tree House at Underhill Hollow
Exterior

2. Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (24 reviews)
"I stayed here for the 2026 Natchaug Epic gravel bike ride, and it was an ideal location, close to the start line. A charming property with a friendly host. "
United States
Mateo A.
The price is AED 463
AED 690 total
includes taxes & fees
31 Aug - 1 Sep
Wizard's Roost at Underhill Hollow
Property grounds

3. SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (17 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is AED 463
AED 690 total
includes taxes & fees
31 Aug - 1 Sep
SteamPunk Bunk House and Intergalactic Way Station
Exterior

4. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (4 reviews)
"Nice, clean and well maintained. Would stay here again."
United States
Sarah S.
The price is AED 841
AED 969 total
includes taxes & fees
31 Aug - 1 Sep
Cottage by the Castle – Downtown Spencer
Property grounds

5. 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
9.2 out of 10, Wonderful, (9 reviews)
"Excellent communicative host with warm welcome and delightful amenities. Quiet neighborhood with plenty of parking."
United States
Pamela L.
The price is AED 605
AED 774 total
includes taxes & fees
1 Sep - 2 Sep
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Coffee/tea maker, fridge, microwave, oven

6. Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
10.0 out of 10, Exceptional, (17 reviews)
"Perfect location"
United States
Harmony F.
The price is AED 1,010
AED 1,900 total
includes taxes & fees
31 Aug - 1 Sep
Spacious 4-bedroom with four and half bathrooms
Interior

7. Angel Sky Challenge

Angel Sky Challenge
Worcester
2.0 out of 10, (1 review)
"The add states an entire home, this is a home with small bedrooms and a bathroom. I was under the impression by the description the entire home was ours without others on the property. I’d put that in the description I felt under comfortable with the men on the property. False advertising "
United States
Cameron R.
The price is AED 588
AED 963 total
includes taxes & fees
31 Aug - 1 Sep
Angel Sky Challenge
Smart TV

8. Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
Shrewsbury
9.4 out of 10, Exceptional, (52 reviews)
"Convenient location for our stay. Great communication by host. Bedrooms were spacious and clean. Large driveway for plenty of parking. Convenient to many shopping options and beautiful park close by. "
United States
Theresa L.
The price is AED 625
AED 1,149 total
includes taxes & fees
31 Aug - 1 Sep
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
Interior

9. Game Room + Bar Lounge, 35 Min to Boston

Game Room + Bar Lounge, 35 Min to Boston
Worcester
The price is AED 790
AED 1,035 total
includes taxes & fees
31 Aug - 1 Sep
Game Room + Bar Lounge, 35 Min to Boston
2 bedrooms, WiFi (free)

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

Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
Shrewsbury
9.4 out of 10, Exceptional, (36 reviews)
"Lovely and great location "
United States
Kimberlee K.
The price is AED 559
AED 1,067 total
includes taxes & fees
21 Sep - 22 Sep
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
Outdoor dining

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

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Ashford
9.6 out of 10, Exceptional, (23 reviews)
"Place was really nice and in a location that made it easy to get back and forth to UCONN. "
United States
Jason C.
The price is AED 658
AED 1,322 total
includes taxes & fees
3 Sep - 4 Sep
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
TV, fireplace

12. Sleeps 15 • Pool • Retreat

Sleeps 15 • Pool • Retreat
Brimfield
10.0 out of 10, Exceptional, (38 reviews)
"It was a beautiful property. Well-tended and all the amenities. Loved the view in morning and evening of mountains and sun / moon."
United States
Daniel C.
The price is AED 3,223
AED 5,967 total
includes taxes & fees
1 Sep - 2 Sep
Sleeps 15 • Pool • Retreat
Property grounds

13. Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6

Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Ware
9.8 out of 10, Exceptional, (24 reviews)
"Nice place to stay a lot of family activities on the premises short distance to shopping and attractions"
United States
Andrew
The price is AED 698
AED 839 total
includes taxes & fees
14 Sep - 15 Sep
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Dining

14. Secluded 2-Acre Lakefront Home! Book Your Getaway!

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (88 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
The price is AED 1,745
AED 2,828 total
includes taxes & fees
1 Sep - 2 Sep
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Terrace/patio

15. Stunning Lakefront Escape! Book Your Dream Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!
Woodstock
10.0 out of 10, Exceptional, (27 reviews)
"We loved our stay at this lakeside retreat. We were in town for a wedding and in between family gatherings we were able to relax by the lake. The house was comfortable and well stocked so we didn't have to buy every little thing. I would definitely stay again"
United States
Lisa R.
The price is AED 1,837
AED 2,945 total
includes taxes & fees
23 Sep - 24 Sep
Stunning Lakefront Escape! Book Your Dream Getaway!
Private kitchen

16. 4-bedroom house in nice Holden with WiFi, AC

4-bedroom house in nice Holden with WiFi, AC
Holden
10.0 out of 10, Exceptional, (1 review)
"The house was located in a quiet, nice, pleasant, neighborhood. The rooms were spacious and comfortable. The house was very clean and the beds were comfortable. The house was located near all kinds of stores, pharmacy’s, and good restaurants. I’d I had to make a negative comment it would be that all the bedrooms were on the second floor which was tough for two of our party. The property owner was quick to respond to questions we had. Overall, a very pleasant stay."
United States
Samantha R.
The price is AED 1,377
AED 2,085 total
includes taxes & fees
1 Sep - 2 Sep
4-bedroom house in nice Holden with WiFi, AC
Private kitchen

17. Modern Farmhouse Close to Mt. Wachusett

Modern Farmhouse Close to Mt. Wachusett
Holden
The price is AED 1,041
AED 2,366 total
includes taxes & fees
31 Aug - 1 Sep
Modern Farmhouse Close to Mt. Wachusett
3 bedrooms, desk, iron/ironing board, WiFi (free)

18. Clifford Luxury Retreat 3BR Self Check In Home

Clifford Luxury Retreat 3BR Self Check In Home
Northbridge
6.8 out of 10, (3 reviews)
"We loved our stay here. The home and the host were both exceptional. We highly recommend this home!"
United States
Martin G.
The price is AED 1,653
AED 1,996 total
includes taxes & fees
31 Aug - 1 Sep
Clifford Luxury Retreat 3BR Self Check In Home
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 Charlton Hotel Reviews

Extended Stay America Suites Boston Westborough Computer Dr

Extended Stay America Suites Boston Westborough Computer Dr

10/10 Excellent
"Ótimo lugar"
Tamires 4-night trip
Posted 10 hours ago
Extended Stay America Suites Boston Westborough Computer Dr