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Holiday Homes in Ashford

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Ashford holiday homes

A window with a view of a grassy field and trees.

1. Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
9.8 out of 10, Exceptional, (7 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 AU$434
includes taxes & fees
14 Oct - 15 Oct
Spacious, unique barn with beautiful views.
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 AU$272
includes taxes & fees
2 Oct - 3 Oct
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 AU$273
includes taxes & fees
2 Oct - 3 Oct
SteamPunk Bunk House and Intergalactic Way Station
A room with a sloped ceiling, wooden beams, a purple door, and a star decoration on the wall.

4. 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 AU$282
includes taxes & fees
4 Oct - 5 Oct
The Tree House at Underhill Hollow
A modern living room with a sofa, a coffee table, and a rug.

5. Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
South Windsor
9.8 out of 10, Exceptional, (10 reviews)
"Good location"
United States
Arthur
The price is AU$175
includes taxes & fees
11 Oct - 12 Oct
Entire guest suite in South Windsor, Connecticut
A dining area with a high ceiling, skylights, and a view of the outdoors.

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

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (93 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
The price is AU$896
includes taxes & fees
1 Nov - 2 Nov
Secluded 2-Acre Lakefront Home! Book Your Getaway!
A modern kitchen with white cabinetry, a wooden island, and a built-in stove.

7. 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 AU$777
includes taxes & fees
4 Oct - 5 Oct
Mohegan Sun Getaway Large Group Retreat
A living room with a staircase, red and grey sofas, a coffee table, and a red door.

8. Modern & Cozy Cape | 4 Bedroom House | Central Location

Modern & Cozy Cape | 4 Bedroom House | Central Location
Manchester Center
9.8 out of 10, Exceptional, (10 reviews)
"Great place"
United States
John S.
The price is AU$441
includes taxes & fees
19 Oct - 20 Oct
Modern & Cozy Cape | 4 Bedroom House | Central Location
A wooden bench and a small wooden bridge in a natural setting with greenery and a stream.

9. 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, (10 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 AU$292
includes taxes & fees
5 Oct - 6 Oct
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
An outdoor seating area with a wood-burning stove, a chair, and a view of a lake.

10. Spacious modern home on private lake

Spacious modern home on private lake
Andover
10.0 out of 10, Exceptional, (29 reviews)
"The lake house was charming, comfortable and well stocked with necessities like towels, blankets, dishes, etc"
United States
Martin G.
The price is AU$554
includes taxes & fees
13 Oct - 14 Oct
Spacious modern home on private lake
A room with a bed, a bookshelf, a TV, a fireplace, and a door leading to another room.

11. 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
9.6 out of 10, Exceptional, (9 reviews)
"This is a real gem of a find! I loved our stay here. GPS does take you to the back of the building but it’s located next to a large parking lot. Plenty of parking which was great for us because we have an extended cab f350 ford that does not fit into most parking spaces. The other great thing about this house is multiple showers and bathrooms. This is so rare in a CT house. I must’ve searched for hours. The host Pam was super friendly and was so quick to respond. The house was super stocked with...
United States
Jenny
The price is AU$508
includes taxes & fees
13 Oct - 14 Oct
Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
A modern dining area with a marble table, white chairs, and a chandelier.

12. Comfy Nest ~ 3BR Sleeps 7 ~ 15 mins to Hartford

Comfy Nest ~ 3BR Sleeps 7 ~ 15 mins to Hartford
Manchester
9.2 out of 10, Wonderful, (5 reviews)
"House was great for our family stay!"
United States
Kim A.
The price is AU$443
includes taxes & fees
4 Oct - 5 Oct
Comfy Nest ~ 3BR Sleeps 7 ~ 15 mins to Hartford
A living room with a TV, sofas, armchairs, and a fireplace.

13. Willow Haven 2BR Cozy Retreat, Close to Hartford

Willow Haven 2BR Cozy Retreat, Close to Hartford
Manchester
8.0 out of 10, Very good, (2 reviews)
"Very friendly and easy to work with host. Communication was excellent. Home was very comfortable and convenient. Would have loved more towels, blankets and pillows. Adding towel hooks in bathroom and second sink area would be excellent. It was a great location."
United States
alissa
The price is AU$661
includes taxes & fees
7 Oct - 8 Oct
Willow Haven 2BR Cozy Retreat, Close to Hartford
A bedroom with a bed, a bedside table, a lamp, and two framed pictures on the wall.

14. Red Door Retreat

Red Door Retreat
Vernon
The price is AU$416
includes taxes & fees
5 Oct - 6 Oct
Red Door Retreat
A modern living room with a flat-screen TV, a glass coffee table, and a staircase leading to another level.

15. Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Manchester
9.2 out of 10, Wonderful, (30 reviews)
"Was a great stay"
United States
John S.
The price is AU$445
includes taxes & fees
21 Oct - 22 Oct
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
A cozy outdoor seating area with a fire feature, two drinks, and hanging plants.

16. Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!

Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!
Webster
10.0 out of 10, Exceptional, (3 reviews)
"We loved the space, it accommodated our larger group and had all the amenities we needed. We only stayed 1 night but would have loved to stay longer! The porch area was very nice to sit out on at night."
United States
Kyle C.
The price is AU$1,243
includes taxes & fees
14 Oct - 15 Oct
Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!
Living area

17. Lakefront Property with Scenic View - All Seasons!

Lakefront Property with Scenic View - All Seasons!
Enfield
10.0 out of 10, Exceptional, (2 reviews)
"My family and I stayed in this lovely cottage the night before our son’s graduation from UConn (approx 49 mins from campus). It was very clean, in a quiet neighborhood and perfect for our needs. Communication with the host was great. We look forward to staying here again in the future."
United States
Diana M.
The price is AU$638
includes taxes & fees
7 Oct - 8 Oct
Lakefront Property with Scenic View - All Seasons!
A spacious living room with a large sectional sofa, wooden flooring, and a high ceiling with skylights.

18. Sleeps 15 • Pool • Retreat

Sleeps 15 • Pool • Retreat
Brimfield
10.0 out of 10, Exceptional, (39 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 AU$2,481
includes taxes & fees
4 Oct - 5 Oct
Sleeps 15 • Pool • Retreat
A modern kitchen with a central island, wooden bar stools, and recessed lighting.

19. Spacious & Newly Renovated Longmeadow Getaway

Spacious & Newly Renovated Longmeadow Getaway
Longmeadow
6.0 out of 10, (3 reviews)
"Great location. Comfortable beds. Good air conditioning."
United States
Matt K.
The price is AU$882
includes taxes & fees
5 Oct - 6 Oct
Spacious & Newly Renovated Longmeadow Getaway
A spacious deck with wicker furniture, large windows offering a view of a lake and trees, and a wooden ceiling.

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

Lake House in Sturbridge w/All the Views!
Sturbridge
9.6 out of 10, Exceptional, (24 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 AU$1,234
includes taxes & fees
4 Oct - 5 Oct
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 Ashford Hotel Reviews

Comfort Inn & Suites Sturbridge - Brimfield

Comfort Inn & Suites Sturbridge - Brimfield

10/10 Excellent
"Excellent"
Maria 1-night trip
Posted 1 hour ago
Comfort Inn & Suites Sturbridge - Brimfield

Find out more about Ashford

Ashford Holiday Homes information

Number of reviews
357
Accommodation
86 Holiday Homes
Lowest Price
AU$175
Highest Price
AU$2,481