A group of hikers on rocky terrain with dense forest in the background.

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Jaffrey holiday homes

A deck with a round table and chairs, surrounded by a white railing, overlooking a lake.

1. 2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.

2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.
Fitzwilliam
10.0 out of 10, Exceptional, (6 reviews)
"Pondlife was clean, calm, cozy, and peaceful...exactly what we wanted...fall foliage was gorgeous....rail trail hiking adjacent to the property and plenty of mountain hiking nearby. If you want to be immersed in nature's beauty, this is perfect..."
United States
Margaret
The price is £223
includes taxes & fees
25 Oct - 26 Oct
2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.
A staircase with a wooden handrail and white steps, leading to a landing with a wooden table and a clock.

2. Enjoy your stay in an antique home in an antique toy museum!

Enjoy your stay in an antique home in an antique toy museum!
Winchendon
9.4 out of 10, Exceptional, (10 reviews)
"What a fun stay! Great communication with the property manager Don, cute town, lots of American history to be discovered, fun stay. 10/10 highly recommend!!!"
United States
Katja Z.
The price is £295
includes taxes & fees
25 Oct - 26 Oct
Enjoy your stay in an antique home in an antique toy museum!
A kitchen with a brick fireplace, wooden cabinets, a central island with stools, and a large window with plants.

3. Cobb Meadow House: Cozy 5 Bedroom Retreat

Cobb Meadow House: Cozy 5 Bedroom Retreat
Dublin
10.0 out of 10, Exceptional, (27 reviews)
"Good place to stay during a wedding week"
United States
Veronique S.
The price is £539
includes taxes & fees
26 Oct - 27 Oct
Cobb Meadow House: Cozy 5 Bedroom Retreat
A conservatory with a view of a lake surrounded by trees. Inside, there are two sofas facing the glass walls.

4. Peaceful Family Friendly Private Lake Waterfront Home Close to Skiing and Hiking

Peaceful Family Friendly Private Lake Waterfront Home Close to Skiing and Hiking
Bennington
10.0 out of 10, Exceptional, (16 reviews)
"Very cozy house Perfect for all family trip Very clean "
United States
Marcin W.
The price is £303
includes taxes & fees
18 Nov - 19 Nov
Peaceful Family Friendly Private Lake Waterfront Home Close to Skiing and Hiking
A hot tub with a wooden deck and a hammock in a backyard.

5. HotTub FirePit Games Huge Backyard Family Friendly

HotTub FirePit Games Huge Backyard Family Friendly
Antrim
9.4 out of 10, Exceptional, (16 reviews)
"The hot tub was great and the peace and quiet was very nice."
United States
Brian B.
The price is £232
includes taxes & fees
25 Oct - 26 Oct
HotTub FirePit Games Huge Backyard Family Friendly
A modern kitchen with granite countertops, stainless steel appliances, and a central island.

6. Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Keene
10.0 out of 10, Exceptional, (4 reviews)
"Communication with the host was easy and the house was great. I would definitely book this home again if/when I come back to Keene."
United States
Jeremy S.
The price is £365
includes taxes & fees
26 Oct - 27 Oct
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
A hot tub on a wooden deck with a staircase leading to an upper level.

7. Rustic & Renovated Hot Tub/Game Room Sleeps 8ppl

Rustic & Renovated Hot Tub/Game Room Sleeps 8ppl
Antrim
9.6 out of 10, Exceptional, (10 reviews)
"Host was communicative and helpful with some specific questions we had. The apartment was in a cute older house, nicely updated and set up for guests. Everything was nicely labeled to be easy to find. The hot tub was great as well!"
United States
Sarah H.
The price is £260
includes taxes & fees
4 Nov - 5 Nov
Rustic & Renovated Hot Tub/Game Room Sleeps 8ppl
A modern kitchen with a wooden countertop, dark cabinets, and a large window.

8. Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
9.4 out of 10, Exceptional, (27 reviews)
"Great stay, clean, accommodating and great location. Will stay again!"
United States
cody s.
The price is £271
includes taxes & fees
28 Oct - 29 Oct
Modern Downtown Escape HotTub Fire Pit Games 12ppl
A hot tub in a rustic interior with wooden beams, a staircase, and seating areas.

9. 16+ppl 2 HotTubs Gamerooms FirePit 2 acre backyard

16+ppl 2 HotTubs Gamerooms FirePit 2 acre backyard
Antrim
10.0 out of 10, Exceptional, (11 reviews)
"Great place to relax with a woody vibe. Excellent stay"
United States
Logan V.
The price is £500
includes taxes & fees
4 Nov - 5 Nov
16+ppl 2 HotTubs Gamerooms FirePit 2 acre backyard
A hot tub with a view of an outdoor area with trees and a wooden structure.

10. Family Friendly, Hot Tub, King Beds Just Renovated

Family Friendly, Hot Tub, King Beds Just Renovated
Hillsborough
The price is £254
includes taxes & fees
25 Oct - 26 Oct
Family Friendly, Hot Tub, King Beds Just Renovated
A house with a deck and a dock extending into a pond, surrounded by autumn foliage.

11. Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston

Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
Stoddard
10.0 out of 10, Exceptional, (6 reviews)
"Everything was perfect for our weekend stay. Host responded immediately to our questions. House had all the amenities for an enjoyable time!"
United States
Mary P.
The price is £466
includes taxes & fees
25 Oct - 26 Oct
Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
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 Jaffrey Hotel Reviews

Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown

8/10 Good
"Not sure why room was so warm. Turned heat off still warm. Had to turn ac on when it's 28 degrees outside. Staff was excellent. Breakfast was good."
Dodge 2-night trip
Posted less than an hour ago
Fairfield Inn & Suites by Marriott Keene Downtown

Find out more about Jaffrey

Jaffrey Holiday Homes information

Number of reviews
133
Accommodation
66 Holiday Homes
Lowest Price
£223
Highest Price
£539