Chester Vacation Rentals
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Our top choices for Chester vacation rentals
1. Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
9.0 out of 10, Wonderful, (1,255 reviews)
"Comfortable stay, well stocked kitchen and room."
Charline
$114 nightly
The price is $128
Dec 5 - Dec 6
Total with taxes and fees
2. Real Estate: Therapy - Lake, Laundry, Love it
Real Estate: Therapy - Lake, Laundry, Love itSherwood 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!"
William C B.
$247 nightly
The price is $276
Nov 9 - Nov 10
Total with taxes and fees
3. 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."
Brian C.
$320 nightly
The price is $357
Nov 5 - Nov 6
Total with taxes and fees
4. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, CanoeingSherwood Forest
9.6 out of 10, Exceptional, (20 reviews)
"Great place and welcoming stay!"
Frank M.
$335 nightly
The price is $374
Nov 5 - Nov 6
Total with taxes and fees
5. Work, Play & Stay! Apt Near Holyoke Medical Center
Work, Play & Stay! Apt Near Holyoke Medical CenterHolyoke
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."
Yvonne A.
$266 nightly
The price is $297
Nov 5 - Nov 6
Total with taxes and fees
6. Modern Studio Ideal for Traveling Professionals
Modern Studio Ideal for Traveling ProfessionalsHolyoke
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"
Kebreab H.
$194 nightly
The price is $217
Nov 8 - Nov 9
Total with taxes and fees
7. Cozy Camper tucked into the woods
Cozy Camper tucked into the woodsSandisfield
10.0 out of 10, Exceptional, (1 review)
"This was a completely hidden gem. I stayed here for one night because I was visiting a friend but I wished I had booked it longer. My friend and I ended up staying here the whole time. I woke up to the sounds of crickets and chickens, and had fresh eggs for breakfast. Then I went for a hike in the pristine woods. Matt and Grace offered to let me use the paddle boards to enjoy the lake! It was a total vacation… no need to go anywhere else. The camper itself was extremely clean and adorably...
hannah w.
$156 nightly
The price is $174
Nov 5 - Nov 6
Total with taxes and fees
8. Modern Studio Ideal for Traveling Professionals
Modern Studio Ideal for Traveling ProfessionalsHolyoke
$208 nightly
The price is $233
Nov 8 - Nov 9
Total with taxes and fees
9. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming DaltonDalton
9.8 out of 10, Exceptional, (35 reviews)
"Very smooth process for check in and directions. Well provisioned, super clean rooms. Really enjoyed learning about Dalton. And so many sights nearby we love!"
Marcia O.
$270 nightly
The price is $301
Nov 10 - Nov 11
Total with taxes and fees
10. Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Beautiful 2-Bedroom + Loft with Hot Tub at Lake AshmereHinsdale
9.8 out of 10, Exceptional, (41 reviews)
"The house was very clean! The hot tub was great! From checking in and checking out the host made everything so easy. We will definitely stay again!"
Kyle R.
$365 nightly
The price is $407
Nov 10 - Nov 11
Total with taxes and fees
11. 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!"
Paula
$237 nightly
The price is $265
Nov 5 - Nov 6
Total with taxes and fees
12. Big farmhouse in the foothills of the Berkshires
Big farmhouse in the foothills of the BerkshiresRussell
10.0 out of 10, Exceptional, (155 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."
Dale B.
$327 nightly
The price is $346
Nov 5 - Nov 6
Total with taxes and fees
13. Peaceful Meadow Retreat
Peaceful Meadow RetreatGranby
10.0 out of 10, Exceptional, (25 reviews)
"Great location, quite country yet close to MA and airport."
Todd R.
$150 nightly
The price is $171
Nov 8 - Nov 9
Total with taxes and fees
14. Button's Modern Luxury Walkup Downtown Northampton
Button's Modern Luxury Walkup Downtown NorthamptonNorthampton
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"
AMY
$426 nightly
The price is $476
Nov 17 - Nov 18
Total with taxes and fees
15. Cozy 2-bedroom apartment in Chicopee
Cozy 2-bedroom apartment in ChicopeeChicopee
10.0 out of 10, Exceptional, (13 reviews)
"nice cozy home in a quiet neighborhood. easy access to highways. would stay here again. "
Christopher P.
$189 nightly
The price is $214
Nov 10 - Nov 11
Total with taxes and fees
16. Cozy Home in Holyoke with 3 bedrooms
Cozy Home in Holyoke with 3 bedroomsHolyoke
9.8 out of 10, Exceptional, (22 reviews)
"Fantastic stay in Holyoke. House is close to town, well outfitted, and super clean. Easy check in process and great experience all around. "
Grant J.
$307 nightly
The price is $343
Dec 1 - Dec 2
Total with taxes and fees
17. Townhouse with Pool Table - Renovated w/ King Bed
Townhouse with Pool Table - Renovated w/ King BedChicopee
10.0 out of 10, Exceptional, (18 reviews)
"Comfortable stay"
Nicholas B.
$370 nightly
The price is $420
Nov 9 - Nov 10
Total with taxes and fees
18. 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 FlagsWest 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...
Jaimie F.
$278 nightly
The price is $318
Nov 9 - Nov 10
Total with taxes and fees
19. 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!"
Nancy M.
$412 nightly
The price is $436
Nov 5 - Nov 6
Total with taxes and fees
20. Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center
Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga CenterLenox
$270 nightly
The price is $302
Nov 5 - Nov 6
Total with taxes and fees
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 Chester Hotel Reviews
The Red Lion Inn
10/10 Excellent
Find out more about Chester
Everything you need to know about Chester vacation rentals
Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 Chester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.
Chester vacation rentals: An excellent choice for every season
Whenever you want to travel, a warm welcome awaits you in Chester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chester in high season.
Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $128 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!
How to find incredible deals on Chester rentals
At Expedia, we put the best Chester vacation 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 Chester 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 Chester vacation.
If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.
