Holiday Homes in Sturbridge

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Check prices for these dates

Our top choices for Sturbridge holiday homes

1. Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!

Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
Sturbridge
9.8 out of 10, Exceptional, (98 reviews)
"very clean, wonderful location"
United States
Anonymous traveller
The price is €410
includes taxes & fees
9 Nov - 10 Nov
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!

2. Lake House in Sturbridge w/All the Views!

Lake House in Sturbridge w/All the Views!
Sturbridge
9.6 out of 10, Exceptional, (25 reviews)
"Pictures don't do this house justice! Great communication from start to finish, very clean house & property, coolest house we've ever stayed at. Hope to stay again!"
United States
Mike T.
The price is €684
includes taxes & fees
9 Nov - 10 Nov
Lake House in Sturbridge w/All the Views!

3. 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, (12 reviews)
"What a beautiful set up for a pet friendly family stay - candles lit upon arrival and a child’s room filled with toys ready to be enjoyed."
United States
Gregory C.
The price is €193
includes taxes & fees
15 Nov - 16 Nov
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8

4. Sleeps 15 • Pool • Retreat

Sleeps 15 • Pool • Retreat
Brimfield
10.0 out of 10, Exceptional, (40 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 €1,570
includes taxes & fees
8 Nov - 9 Nov
Sleeps 15 • Pool • Retreat

5. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (9 reviews)
"Nice, clean and well maintained. Would stay here again."
United States
Sarah S.
The price is €203
includes taxes & fees
8 Nov - 9 Nov
Cottage by the Castle – Downtown Spencer

6. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (46 reviews)
"Nice place to stay has good air conditioning "
United States
Zachary P.
The price is €169
includes taxes & fees
8 Nov - 9 Nov
The Tree House at Underhill Hollow

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

Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Ware
9.6 out of 10, Exceptional, (28 reviews)
"This was a super cozy ,cute place to stay . Host had muffins , juice and milk for us. The property was quiet and very peaceful."
United States
theresa H.
The price is €169
includes taxes & fees
9 Nov - 10 Nov
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6

8. Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (26 reviews)
"Great stay!!"
United States
Elizabeth G.
The price is €163
includes taxes & fees
8 Nov - 9 Nov
Wizard's Roost at Underhill Hollow

9. SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (20 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is €163
includes taxes & fees
8 Nov - 9 Nov
SteamPunk Bunk House and Intergalactic Way Station

10. Bling nest

Bling nest
Ludlow
The price is €358
includes taxes & fees
7 Nov - 8 Nov
Bling nest

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

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (95 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
The price is €545
includes taxes & fees
10 Nov - 11 Nov
Secluded 2-Acre Lakefront Home! Book Your Getaway!

12. Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
9.8 out of 10, Exceptional, (23 reviews)
"Great, clean location to stay."
United States
Mike O.
The price is €430
includes taxes & fees
8 Nov - 9 Nov
Spacious 4-bedroom with four and half bathrooms

13. 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 €212
includes taxes & fees
9 Nov - 10 Nov
Angel Sky Challenge

14. Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
Boston Road
8.8 out of 10, Excellent, (25 reviews)
"The stove was broken, which we were made aware of and there was an offer to cancel for us. We chose to still go because we needed a place to stay. The stove was in the middle of the kitchen when we arrived. I did decide to cancel the second night in the owner, said they would refund us, but they only refund part of the second night."
United States
Gladys B.
The price is €336
includes taxes & fees
9 Nov - 10 Nov
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

15. Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants

Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
Somers
9.8 out of 10, Exceptional, (12 reviews)
"Fantastic host. Went out of their way to make our stay very pleasant. Beautiful historic home that felt very welcoming and cozy even though it is so big!"
United States
John
The price is €316
includes taxes & fees
17 Nov - 18 Nov
Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants

16. Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC

Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC
Boston Road
9.0 out of 10, Wonderful, (14 reviews)
"Our stay was fantastic. Check in was super smooth and the host was very responsive. I would definitely stay here again in the future."
United States
Nicholas T.
The price is €322
includes taxes & fees
9 Nov - 10 Nov
Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC

17. The Christmas Cottage, 4BR New England Escape

The Christmas Cottage, 4BR New England Escape
Rutland
The price is €663
includes taxes & fees
8 Nov - 9 Nov
The Christmas Cottage, 4BR New England Escape

18. Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
10.0 out of 10, Exceptional, (11 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 €265
includes taxes & fees
8 Nov - 9 Nov
Spacious, unique barn with beautiful views.

19. Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston

Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston
Worcester
8.0 out of 10, Very good, (1 review)
"The house was fine overall. There were just a few things that stood out - only 3 towels but we were 4, no baking sheet for the oven, lighting in the kitchen wasn’t great, couldn’t find the house or unit number and the lock box was hard to find. The main bed was very comfortable but the pillows were not."
United States
Laura P.
The price is €285
includes taxes & fees
7 Nov - 8 Nov
Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston

20. 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, (3 reviews)
"Communication with owner was very responsive and timely. House was clean and as description. Any problems were immediately addressed by owner."
United States
larry d.
The price is €476
includes taxes & fees
7 Nov - 8 Nov
4-bedroom house in nice Holden with WiFi, AC
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.

Sturbridge and related destinations

Step back in time at Old Sturbridge Village where costumed interpreters bring 1830s New England to life. Explore nearby Hyland Orchards for apple picking in fall, or paddle along the Quinebaug River when summer's warmth arrives.

A rural farm with stone walls, wooden barns, and a cow in a fenced area.