A red barn with a metal roof, surrounded by a snow-covered landscape and a wooden fence.

Guest Houses in Hampshire County

Compare and save

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
11 Sep - 13 Sep
In two weeks
18 Sep - 20 Sep
In one month
2 Oct - 4 Oct
In two months
30 Oct - 1 Nov

Our top choices for Hampshire County guest houses

BBQ/picnic Area

1. Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (50 reviews)
"Enjoyed the games and record players in all rooms including amazing collection of albums in main living area. Rooms are nice. Tight on parking. Great location. We would stay here again."
United States
Ann
The price is 3.650.360 ₫
4.077.452 ₫ total
includes taxes & fees
7 Sept - 8 Sept
Hideaway Inn Lenox
Exterior

2. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.4 out of 10, Very good, (406 reviews)
"Large, clean, comfortable suite."
United States
Rena
The price is 2.581.326 ₫
2.883.263 ₫ total
includes taxes & fees
7 Sept - 8 Sept
The Central Downtown Inn & Suites
55-inch LCD TV with digital channels, printers

3. The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (37 reviews)
"Great place. Large rooms amazing common areas super fun w friends. "
United States
James
The price is 4.317.854 ₫
4.823.168 ₫ total
includes taxes & fees
20 Sept - 21 Sept
The Revival House
Front of property

4. Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (149 reviews)
"Lovely Victorian house on a quiet street. Only a few blocks from the center of the town of Shelburne Falls, which is a charming New England town with a lovely river and a beautiful "bridge of flowers.""
United States
steven
The price is 2.745.592 ₫
4.344.452 ₫ total
includes taxes & fees
16 Sept - 17 Sept
Blooming Inn
Lounge

5. The Dewey

The Dewey
3.5 star property
Lenox
8.6 out of 10, Excellent, (330 reviews)
"There is no staff on site. Fire alarm went off no one showed up for 20 mins. The shower situation was less than desirable. The property outside was not weeded and lacked any care. Any guest that I spoke to all felt the same. We go once a year to Lenox and will not be staying there."
United States
Casey
The Dewey
Miscellaneous

6. Sturbridge Country Inn

Sturbridge Country Inn
2.5 star property
Fiskdale
4.8 out of 10, (116 reviews)
"the staff was very welcoming took us to our room explained how the fire place and hot tub worked a very enjoyable relaxing stay"
United States
Russell
The price is 6.518.500 ₫
7.281.165 ₫ total
includes taxes & fees
6 Sept - 7 Sept
Sturbridge Country Inn
Comfort House, 4 Bedrooms, Non Smoking | Private kitchen | Coffee/tea maker, full-sized fridge, microwave, oven

7. Upscaled Home in a Quiet Neighborhood

Upscaled Home in a Quiet Neighborhood
3.0 star property
Forest Park
8.4 out of 10, Very good, (5 reviews)
"So clean and comfy"
United States
Anonymous traveller
Upscaled Home in a Quiet Neighborhood
Fireplace

8. Jacob's Tanglewood Ranch

Jacob's Tanglewood Ranch
3.0 star property
Lee
Jacob's Tanglewood Ranch
Interior

9. Chestnut Lodge

Chestnut Lodge
3.5 star property
Lee
2.0 out of 10, (2 reviews)
"An absolutely horrible experience! My family (2 adults and my 6 year old son) had reserved this so-called hotel for $284 in June for a 13th Aug stay. After a full day at the Berkshires, we checked-in at 6 pm. This place is in a terrible location (unpaved roads, still-in construction steps). To our horror we found that the room had No Air-Conditioning. It was 90 degrees outside and all they had in the room was a ceiling fan. There were bugs in the room due to the heat. On top of it all the...
United States
Priya
Chestnut Lodge
Fitness facility

10. Angels Rest Retreat

Angels Rest Retreat
3.0 star property
Leyden
10.0 out of 10, Exceptional, (1 review)
"Angel's Rest is sooo peaceful. We had a delicious and super healthy breakfast in the breakfast nook, surrounded by lovely plants and a small fountain, looking out over the rolling hills of Western Mass. The fall colors were nice. "
United States
Sharon
Angels Rest Retreat
Basic Room | Iron/ironing board, free WiFi

11. YLD Rooms Rome - Shared Bath & Spaces

YLD Rooms Rome - Shared Bath & Spaces
2.0 star property
Forest Park
YLD Rooms Rome - Shared Bath & Spaces
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Hampshire County Hotel Reviews

Holiday Inn Express Springfield Downtown by IHG

Holiday Inn Express Springfield Downtown by IHG

10/10 Excellent
"I was greeted by Selena and her friendly professional staff at check in! They went above and beyond to accommodate me and my family by trying to get us checked in before 4pm since we were traveling from afar! The rooms were clean, nice bedding, soft pillows, and excellent buffet breakfast! I even enjoyed the soap they had in the bathroom so much that I ordered it as soon as I got home! The parking garage is currently under construction but we were still accommodated which was perfect! We plan to visit again soon and looking forward to another wonderful experience!"
Dorothy 1-night trip
Posted 1 hour ago
Holiday Inn Express Springfield Downtown by IHG

Find out more about Hampshire County

Hampshire County Guest Houses information

Number of reviews
1,041
Accommodation
10 Guest Houses
Lowest Price
2.883.263 ₫
Highest Price
7.281.165 ₫