A white building with a clock tower, surrounded by a garden of red and white flowers.

Holiday Homes in Oxford

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Oxford holiday homes

A room with a sloped ceiling, wooden beams, a purple door, and a star decoration on the wall.

1. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (42 reviews)
"Great space, lots of fun."
United States
Douglas C.
The price is €174
includes taxes & fees
7 Oct - 8 Oct
The Tree House at Underhill Hollow
A red building with a colorful mural on the front, a covered porch, and a stone foundation.

2. Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (26 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 €169
includes taxes & fees
27 Sept - 28 Sept
Wizard's Roost at Underhill Hollow
A rustic building with a brick exterior and a red roof, situated next to a pond with tall reeds and a tree with autumn-colored leaves.

3. SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (18 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is €168
includes taxes & fees
7 Oct - 8 Oct
SteamPunk Bunk House and Intergalactic Way Station

4. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (7 reviews)
"The cottage is beautiful, cozy and super comfortable! We loved it! The hosts also were super, communicative and friendly. The place was clean, we had everything we needed, is in a very safe area, and very pretty! Hight recommended! Thank you for hosting us!"
United States
Fabiola
The price is €214
includes taxes & fees
28 Sept - 29 Sept
Cottage by the Castle – Downtown Spencer
A bedroom with a large mirror, a bed with floral bedding, a standing lamp, and a window with curtains.

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

Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
Shrewsbury
9.6 out of 10, Exceptional, (37 reviews)
"Lovely and great location "
United States
Kimberlee K.
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
A bedroom with a large bed, a desk, a chair, a mirror, and a clock on the wall.

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

Game Room + Bar Lounge, 35 Min to Boston
Worcester
The price is €240
includes taxes & fees
27 Sept - 28 Sept
Game Room + Bar Lounge, 35 Min to Boston
A living room with a sofa, a clock, a floor lamp, and a rug.

7. Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
Shrewsbury
9.4 out of 10, Exceptional, (54 reviews)
"Amazing host and fabulous spacious property. "
United States
Kelly L.
The price is €265
includes taxes & fees
13 Oct - 14 Oct
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
A compact, modern laundry room with a built-in washer and dryer, a small storage cabinet, and a tiled floor.

8. 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 €235
includes taxes & fees
25 Sept - 26 Sept
Angel Sky Challenge
A modern kitchen with a stainless steel refrigerator, double sink, and wooden flooring.

9. Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
10.0 out of 10, Exceptional, (21 reviews)
"Perfect location"
United States
Harmony F.
The price is €441
includes taxes & fees
27 Sept - 28 Sept
Spacious 4-bedroom with four and half bathrooms
A deck with red Adirondack chairs, a grill, and a view of trees and sunset.

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

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Ashford
9.6 out of 10, Exceptional, (25 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 €300
includes taxes & fees
28 Sept - 29 Sept
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
A cozy outdoor seating area with a fire feature, two drinks, and hanging plants.

11. 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 €565
includes taxes & fees
14 Oct - 15 Oct
Family-friendly 2- Bedroom Webster Home w/Cozy Balcony
A wooden bench and a small wooden bridge in a natural setting with greenery and a stream.

12. 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)
"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 €170
includes taxes & fees
28 Sept - 29 Sept
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
A cozy attic bedroom with a skylight, a piano, a mirror, and a bedside table with a lamp.

13. Clifford Luxury Retreat 3BR Self Check In Home

Clifford Luxury Retreat 3BR Self Check In Home
Northbridge
8.4 out of 10, Very good, (6 reviews)
The price is €468
includes taxes & fees
27 Sept - 28 Sept
Clifford Luxury Retreat 3BR Self Check In Home
A residential property with a grassy yard, a tree, and a house in the background.

14. Renovated Lakefront 5BR • Near Colleges • Sunsets • Sleeps 12

Renovated Lakefront 5BR • Near Colleges • Sunsets • Sleeps 12
Worcester
The price is €612
includes taxes & fees
13 Oct - 14 Oct
Renovated Lakefront 5BR • Near Colleges • Sunsets • Sleeps 12
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

15. 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, (2 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 €487
includes taxes & fees
27 Sept - 28 Sept
4-bedroom house in nice Holden with WiFi, AC
A modern kitchen with white cabinetry, a wooden island, and a built-in stove.

16. Mohegan Sun Getaway Large Group Retreat

Mohegan Sun Getaway Large Group Retreat
Killingly
7.4 out of 10, Good, (3 reviews)
"Great setup. Perfect crash pad for a weekend of the Natchaug Epic bike race in Thompson… slept 8 no problem. Host was helpful and beds were clean, kitchens were just what we needed"
United States
shawn c b.
The price is €542
includes taxes & fees
28 Sept - 29 Sept
Mohegan Sun Getaway Large Group Retreat
A modern interior with a kitchen, dining area, and living space.

17. 6 Beds Home w/Game Room Perfect for Groups

6 Beds Home w/Game Room Perfect for Groups
Killingly
The price is €566
includes taxes & fees
28 Sept - 29 Sept
6 Beds Home w/Game Room Perfect for Groups
A spacious deck with wicker furniture, large windows offering a view of a lake and trees, and a wooden ceiling.

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

Lake House in Sturbridge w/All the Views!
Sturbridge
9.6 out of 10, Exceptional, (23 reviews)
"We really appreciated the kindling and firewood for the outdoor fire pit.The house was clean and nice."
United States
Christian C.
The price is €698
includes taxes & fees
27 Sept - 28 Sept
Lake House in Sturbridge w/All the Views!
A dining area with a high ceiling, skylights, and a view of the outdoors.

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

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (92 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
The price is €674
includes taxes & fees
27 Sept - 28 Sept
Secluded 2-Acre Lakefront Home! Book Your Getaway!
A modern kitchen with white cabinetry, a large island, and pendant lighting.

20. Modern Farmhouse Close to Mt. Wachusett

Modern Farmhouse Close to Mt. Wachusett
Holden
The price is €578
includes taxes & fees
7 Oct - 8 Oct
Modern Farmhouse Close to Mt. Wachusett
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 Oxford Hotel Reviews

DoubleTree by Hilton Hotel Boston - Westborough

DoubleTree by Hilton Hotel Boston - Westborough

10/10 Excellent
"Clean room and friendly staff made it a wonderful experience."
Heather 1-night trip
Posted 1 hour ago
DoubleTree by Hilton Hotel Boston - Westborough

Find out more about Oxford

Oxford Holiday Homes information

Number of reviews
371
Accommodation
111 Holiday Homes
Lowest Price
€168
Highest Price
€698