Condo Rentals in Hampshire County

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Check prices for these dates

Next weekend
23 Jan - 25 Jan
In two weeks
30 Jan - 1 Feb
In one month
13 Feb - 15 Feb
In two months
13 Mar - 15 Mar

Top Cities in Hampshire County

Main Street Stroll
Condo RentalsCondo Rentals

Northampton

Northampton

Our top choices for Hampshire County condo rentals

Lobby

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,209 reviews)
"I great place to stay!!"
United Kingdom
Maricel
The price is AED 382
AED 467 total
includes taxes & fees
19 Jan - 20 Jan
Vacation Village in the Berkshires
A heated pool

Club Wyndham Bentley Brook Resort - 2 Bedroom

Club Wyndham Bentley Brook Resort - 2 Bedroom
Hancock
8.4 out of 10, Very Good, (6 reviews)
"Great spot for family ski trip. Location was great. Condo and amenities were great. Overall super happy and would stay again. "
United States
Ellamae G.
Club Wyndham Bentley Brook Resort - 2 Bedroom
Exterior

Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool

Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool
Hancock
10.0 out of 10, Exceptional, (3 reviews)
"Good base for Berkshires, responsive host, good rates, secure."
United States
Robert
Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool
Fridge, microwave, oven, stovetop

SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!

SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
Hancock
10.0 out of 10, Exceptional, (14 reviews)
"Perfect spot to relax!"
United States
Tisha C.
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
Outdoor dining

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Hancock
7.2 out of 10, Good, (11 reviews)
"Perfect spot for Mountain Adventures, property was well equipped with comfortable necessities. It was very clean and spacious for six people, 3 adults and 3 young boys. We would definitely stay again. "
United States
PK N.
The price is AED 529
AED 1,280 total
includes taxes & fees
26 Jan - 27 Jan
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Exterior

Tranquil Lakeside Escape in the Berkshires

Tranquil Lakeside Escape in the Berkshires
Lenox
10.0 out of 10, Exceptional, (1 review)
"perfect location to go everywhere in the Berkshires"
United States
Edward G.
Tranquil Lakeside Escape in the Berkshires
Property grounds

SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2

SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2
Hancock
10.0 out of 10, Exceptional, (36 reviews)
"Great location and fabulous host, very helpful and kind."
United States
Richard H.
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2
Property grounds

SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1

SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
Hancock
10.0 out of 10, Exceptional, (41 reviews)
"3rd time staying here. The host is great, the place is clean, and the location couldn't be better!"
United States
Dan H.
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
Exterior

Escape to the Heart of Jiminy Peak: Country Inn condo with full kitchen, 2 bths

Escape to the Heart of Jiminy Peak: Country Inn condo with full kitchen, 2 bths
Hancock
10.0 out of 10, Exceptional, (1 review)
"The clean room was very comfortable and we enjoyed the mountain view"
United States
Susan C.
Escape to the Heart of Jiminy Peak: Country Inn condo with full kitchen, 2 bths
4 bedrooms, iron/ironing board, WiFi, bed sheets

Spacious 4-bedroom condo with AC and WiFi in charming Enfield

Spacious 4-bedroom condo with AC and WiFi in charming Enfield
Enfield
10.0 out of 10, Exceptional, (2 reviews)
"I had a family event in the area and needed a place for 8 people that was of better value than hotel rooms. This location was the perfect option."
United States
Logan M.
Spacious 4-bedroom condo with AC and WiFi in charming Enfield
Interior

UNIQUE - 1BR Country Condo @ Jiminy Peak

UNIQUE - 1BR Country Condo @ Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (14 reviews)
"lovely place to stay"
United States
Nancy P.
The price is AED 592
AED 1,428 total
includes taxes & fees
8 Feb - 9 Feb
UNIQUE - 1BR Country Condo @ Jiminy Peak
Pool

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Hancock
9.0 out of 10, Wonderful, (2 reviews)
"very nice and roomy! really enjoyed."
United States
Shack M.
The price is AED 503
AED 1,104 total
includes taxes & fees
28 Jan - 29 Jan
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Outdoor dining

3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY

3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY
Hancock
9.6 out of 10, Exceptional, (17 reviews)
"Perfect place for our annual ski-cation. Great accommodations minutes from Jiminy Peak. Equipped with everything you need for a great vacation!"
United States
Nancy S.
3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY
Exterior

Peaceful 1BR Condo with Pond View

Peaceful 1BR Condo with Pond View
Lenox
8.0 out of 10, Very Good, (2 reviews)
"Beautiful grounds and views and so close to Tanglewood! We had a great time. Apartment was clean and very private. It was quiet and quaint.The only issue I should mention is the carpeting; seemed a bit dump and not very appealing."
United States
Maria C.
Peaceful 1BR Condo with Pond View
Property grounds

Welcome to Honey Spot!

Welcome to Honey Spot!
Pine Point
9.8 out of 10, Exceptional, (27 reviews)
"Ricardo was a great!!made are stay wonderful was very helpful and went out of his way to make or stay great we had a good time place was beautiful something for everyone will definitely stay here again thank u"
United States
Marie A.
The price is AED 477
AED 1,092 total
includes taxes & fees
28 Jan - 29 Jan
Welcome to Honey Spot!
Exterior

Ski-In/Ski-Out at Jiminy Peak in the Country Inn

Ski-In/Ski-Out at Jiminy Peak in the Country Inn
Hancock
9.0 out of 10, Wonderful, (27 reviews)
"We had a great experience with this rental. Nice location for skiing on and off the mountain and close to the heart of the ski facility. "
United States
Nicole S.
Ski-In/Ski-Out at Jiminy Peak in the Country Inn
Dining

Charming 3-bedroom condo with WiFi in Williamstown, MA

Charming 3-bedroom condo with WiFi in Williamstown, MA
Williamstown
Charming 3-bedroom condo with WiFi in Williamstown, MA
Interior

Cozy nest of a condo tiny home in Downtown Northampton-- walk to Smith College!

Cozy nest of a condo tiny home in Downtown Northampton-- walk to Smith College!
Northampton
10.0 out of 10, Exceptional, (1 review)
"I really enjoyed my stay at this Vrbo. Everything was well stocked (bedroom/bathroom/kitchen linens, cleaning supplies, kitchen appliances / serveware etc). The futon pulled out was comfortable. The flat is in a great location that is walking-distance to cafes/restaurants. Tre was an excellent host!"
United States
Anonymous traveler
Cozy nest of a condo tiny home in Downtown Northampton-- walk to Smith College!
Exterior

Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5

Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5
Hancock
9.8 out of 10, Exceptional, (7 reviews)
"It was exactly as described, perfect for a family stay with easy ski on and off. I was pleasantly surprised with all the amenities of the property. Would stay again!"
United States
Christine O.
Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5
Interior

Thanksgiving Mountain Lodge, Mass.- 1 BR 1 Ba. Bousquet Mt Ski 11/26-11/29/2025

Thanksgiving Mountain Lodge, Mass.- 1 BR 1 Ba. Bousquet Mt Ski 11/26-11/29/2025
Pittsfield
8.0 out of 10, Very Good, (1 review)
"Convenient location. Noisy guests in room above ours. "
United States
Anne C.
Thanksgiving Mountain Lodge, Mass.- 1 BR 1 Ba. Bousquet Mt Ski 11/26-11/29/2025
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 Hampshire County Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Clean, very nice bed and linens, pool, jacuzzi, in room fireplace. Balcony right outside of living room. The breakfast was ok, they offered a lot but not top quality. The waffles were very good and the bacon. Overall excellent stay. Conveniently located to everything."
James 2-night trip
Posted 2 days ago
The Yankee, Trademark Collection by Wyndham

Frequently asked questions

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