Westhampton Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Westhampton holiday rentals

A two-story house with a front porch, a sign reading "Victory Residence," and the address "1785."

1. Modern Studio Ideal for Traveling Professionals

Modern Studio Ideal for Traveling Professionals
Holyoke
10.0 out of 10, Exceptional, (4 reviews)
"The room was very clean and modern. The check-in process was easy and I had the best rest that I had in a long time. Being in the lower level with no windows provided a very quiet and dark ambiance at night. There is ample lighting throughout the unit if needed though, you can really unplug here. I would definitely stay here again"
United States
Kebreab H.
The price is AU$334
includes taxes & fees
16 Nov - 17 Nov
Modern Studio Ideal for Traveling Professionals
Exterior

2. Work, Play & Stay! Apt Near Holyoke Medical Center

Work, Play & Stay! Apt Near Holyoke Medical Center
Holyoke
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful apartment! Amazing finishes, well appointed, pristine apartment in Holyoke. Great communication from the host. A quick trip to Dam Coffee Shop for great coffee and breakfast options. Not too far from Stop & Shop for food and short ride to highway. Would book this spot again."
United States
Yvonne A.
The price is AU$439
includes taxes & fees
22 Nov - 23 Nov
Work, Play & Stay! Apt Near Holyoke Medical Center
A two-story house with a front porch, a sign reading "Victory Residence," and the address "1785."

3. Modern Studio Ideal for Traveling Professionals

Modern Studio Ideal for Traveling Professionals
3.0 star property
Holyoke
The price is AU$340
includes taxes & fees
16 Nov - 17 Nov
Modern Studio Ideal for Traveling Professionals
A hot tub on a wooden deck with snow on the ground and trees in the background.

4. The Creation Station is a cozy place so make yourself at home.

The Creation Station is a cozy place so make yourself at home.
Easthampton Ma.
10.0 out of 10, Exceptional, (79 reviews)
"We had such a great stay at the Creation Station! The host John, showed us around the property and explained how to use everything. He also recommended a great restaurant in town. It was a great experience and would definitely recommend it!"
United States
Paula
The price is AU$388
includes taxes & fees
19 Nov - 20 Nov
The Creation Station is a cozy place so make yourself at home.
A spacious living room with a wooden staircase, a dining area, and a television.

5. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.6 out of 10, Exceptional, (4 reviews)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
The price is AU$415
includes taxes & fees
26 Nov - 27 Nov
Real Estate: Therapy - Lake, Laundry, Love it
A two-story house with a front porch, a concrete walkway, and a well-maintained lawn.

6. Cozy Home in Holyoke with 3 bedrooms

Cozy Home in Holyoke with 3 bedrooms
Holyoke
9.8 out of 10, Exceptional, (22 reviews)
"The house was lovely and clean and the location was very convenient for us. We would stay there again!"
United States
Jennifer S.
The price is AU$476
includes taxes & fees
6 Dec - 7 Dec
Cozy Home in Holyoke with 3 bedrooms
A modern kitchen with a central island, bar stools, and a bicycle.

7. Button's Modern Luxury Walkup Downtown Northampton

Button's Modern Luxury Walkup Downtown Northampton
Northampton
10.0 out of 10, Exceptional, (8 reviews)
"The apartment was very comfortable and had everything we needed for the weekend including nice coffee, cava and a treat. Well equipped kitchen and good bed, towels, storage. Will stay here again"
United States
AMY
The price is AU$685
includes taxes & fees
18 Nov - 19 Nov
Button's Modern Luxury Walkup Downtown Northampton
A living room with a fireplace, a sofa, a coffee table, and a TV.

8. Cozy 2-bedroom apartment in Chicopee

Cozy 2-bedroom apartment in Chicopee
Chicopee
10.0 out of 10, Exceptional, (13 reviews)
"nice cozy home in a quiet neighborhood. easy access to highways. would stay here again. "
United States
Christopher P.
The price is AU$317
includes taxes & fees
17 Nov - 18 Nov
Cozy 2-bedroom apartment in Chicopee
A modern fireplace with a glass enclosure, decorative items, and a sign that reads 'blessed.'

9. A Scenic Townhouse Near Amherst (Next to a Horse Farm)

A Scenic Townhouse Near Amherst (Next to a Horse Farm)
Sunderland
10.0 out of 10, Exceptional, (1 review)
"Great place! Very clean!"
United States
Sherry T.
The price is AU$428
includes taxes & fees
16 Nov - 17 Nov
A Scenic Townhouse Near Amherst (Next to a Horse Farm)
A red barn with a black door and a heart-shaped cutout, surrounded by lush greenery and trees.

10. Charming, updated 3 bedroom farmhouse farm stay.

Charming, updated 3 bedroom farmhouse farm stay.
Williamsburg
10.0 out of 10, Exceptional, (44 reviews)
"Wonderful place to stay with our two teens. We visited family in Amherst, looked at colleges and had a great time touring historic sites. Definitely recommend!"
United States
Nancy M.
The price is AU$573
includes taxes & fees
6 Dec - 7 Dec
Charming, updated 3 bedroom farmhouse farm stay.
A television displaying a coastal scene, a window with a view of buildings, and a sign reading 'CAPE COD'.

11. Penthouse overlooking downtown Amherst!

Penthouse overlooking downtown Amherst!
Amherst
10.0 out of 10, Exceptional, (2 reviews)
"Great space. Great location."
United States
Mike S.
The price is AU$782
includes taxes & fees
13 Nov - 14 Nov
Penthouse overlooking downtown Amherst!
A hot tub with a string of lights above it, set against a dark night sky.

12. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.6 out of 10, Exceptional, (20 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is AU$538
includes taxes & fees
13 Nov - 14 Nov
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A living room with a sofa set, a coffee table, and two lamps.

13. Cozy First Floor Apartment. Located in a quiet neighborhood.

Cozy First Floor Apartment. Located in a quiet neighborhood.
Chicopee
9.6 out of 10, Exceptional, (14 reviews)
"Check in was very easy. The apartment had all the necessities in the kitchen and bathroom. Location was convenient and the neighborhood very safe/quiet."
United States
Morrris
The price is AU$445
includes taxes & fees
29 Nov - 30 Nov
Cozy First Floor Apartment. Located in a quiet neighborhood.
A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a pool table.

14. Townhouse with Pool Table - Renovated w/ King Bed

Townhouse with Pool Table - Renovated w/ King Bed
Chicopee
10.0 out of 10, Exceptional, (20 reviews)
"Comfortable stay"
United States
Nicholas B.
The price is AU$607
includes taxes & fees
18 Nov - 19 Nov
Townhouse with Pool Table - Renovated w/ King Bed
A triangular-shaped building with a balcony and a wooden picnic table in front.

15. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (10 reviews)
"My wife and I had a lovely time staying here. Great location, only a couple of miles away from Jacobs Pillow. The lakes are clean and great for paddle boarding. Check in and out was a breeze, Nicole was a pleasure to work with. Thanks for a nice get away."
United States
Brian C.
The price is AU$513
includes taxes & fees
15 Nov - 16 Nov
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A blue house with a porch, a wooden bench, and a door.

16. Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Greenfield
9.4 out of 10, Exceptional, (11 reviews)
"Very satisfied with the stay . Clean quiet and relaxing stay."
United States
JAMES S.
The price is AU$336
includes taxes & fees
18 Nov - 19 Nov
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
A single-story house with a red front door, white siding, and a brick chimney.

17. Red Door Retreat West Springfield 3 bedroom w/ Game Room! Near Big E & Six Flags

Red Door Retreat West Springfield 3 bedroom w/ Game Room! Near Big E & Six Flags
West Springfield
10.0 out of 10, Exceptional, (1 review)
"Adorable home, set up so cute plus being pet friendly means everything to me when deciding. All was as described and our host had everything you could need and more available to us in the well stocked kitchen and bathroom. Very quiet safe and friendly neighborhood on a dead end street, gated walkway as well as a gated driveway made me feel plenty safe enough to take my dog out at night. Bedrooms were welcoming and set up with pretty fairy lights throughout, all three beds were very comfortable...
United States
Jaimie F.
The price is AU$458
includes taxes & fees
12 Dec - 13 Dec
Red Door Retreat West Springfield 3 bedroom w/ Game Room! Near Big E & Six Flags
A white porch with two rocking chairs, a door, and a number '205'.

18. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (156 reviews)
"Great place and stunning location. Absolutely loved the quiet and perfect mix of old times with modern convenience. Had a short stay this trip but intend on returning in the future."
United States
Dale B.
The price is AU$498
includes taxes & fees
15 Nov - 16 Nov
Big farmhouse in the foothills of the Berkshires
A two-story house with a front porch, a staircase leading to the entrance, and a well-maintained garden.

19. 2 Twin beds on 1st floor with En-suite bathroom.

2 Twin beds on 1st floor with En-suite bathroom.
Shelburne Falls
The price is AU$251
includes taxes & fees
15 Nov - 16 Nov
2 Twin beds on 1st floor with En-suite bathroom.
A gazebo with seating, surrounded by a fenced area with trees and a clear sky.

20. Serene 1-bedroom suite on 75 acre horse property

Serene 1-bedroom suite on 75 acre horse property
Belchertown
10.0 out of 10, Exceptional, (40 reviews)
"We had a great, restorative stay in Liberty Woods. It is a lovely oasis with kind humans, friendly animals and beautiful horses in a beautiful setting."
United States
Anna O.
The price is AU$378
includes taxes & fees
30 Nov - 1 Dec
Serene 1-bedroom suite on 75 acre horse property
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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Find holiday rentals that suit your style

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Top Westhampton Hotel Reviews

An outdoor patio area with seating, a fire feature, and a view of the building's exterior.
Courtyard by Marriott West Springfield

Courtyard by Marriott West Springfield

Courtyard by Marriott West Springfield
West Springfield

8/10 Good

The room smelt a bit musty/BO s and the shower head was terrible. Good guest laundry facilities, bed was super comfy and room was generally clean. Wifi was moderate. Location handy for nearby suburbs and close to shops.
Australia
Clinton
Reviewed October 13, 2026
Courtyard by Marriott West Springfield

Find out more about Westhampton

Everything you need to know about Westhampton holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Westhampton holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Westhampton holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Westhampton holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Westhampton. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Westhampton holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Westhampton holiday rentals we have selected for you start as low as AU$317 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Westhampton rentals

At Expedia, we put the best Westhampton holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Westhampton rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Westhampton holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Westhampton. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Are there holiday rentals in Westhampton?

Yes, there are holiday rentals close to the most popular sights in Westhampton, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Westhampton has to offer?

Experience Three Sisters Sanctuary in Goshen, MA: This holiday home rental outside of Westhampton is equipped with a garden, air conditioning and a Smart TV to help you feel comfortable during your stay.

What can I see and do in Westhampton?

Duck Island and Pine Island are a couple of lovely local spots to get outside and enjoy nature. Westhampton Town Hall and Westhampton Memorial Library are other places to visit while you're in town.

What are holiday rentals like in Westhampton?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Westhampton. Holiday rentals offer extras like kitchens and laundry facilities so you'll have everything you want. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from shared hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for a family trip or a small group gathering.