Chester Vacation Rentals from $302: Search Short-Term Rentals

Q: What are some of the best vacation rentals that Chester has to offer?

Cozy Riverside Berkshires Retreat : You might want to consider this vacation home rental near Chester, which is located on a river and has a fireplace, a garden, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and kitchenware, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Chester vacation rentals

Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke

Holyoke

$242 nightly

Jun 5 - Jun 6

Total with taxes and fees

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

Sherwood Forest

Sharon K.

$337 nightly

Jun 10 - Jun 11

Total with taxes and fees

Nurse-Ready Studio Retreat! 2 Mi to Dtwn Holyoke

Holyoke

Michelle

$246 nightly

Jun 5 - Jun 6

Total with taxes and fees

1 bedroom, desk, iron/ironing board, travel crib

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

Easthampton Ma.

Christopher K.

$246 nightly

Jun 22 - Jun 23

Total with taxes and fees

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

Sherwood Forest

Frank M.

$348 nightly

Jun 7 - Jun 8

Total with taxes and fees

Peaceful Meadow Retreat

Granby

Kaleigh L.

$182 nightly

Jun 14 - Jun 15

Total with taxes and fees

Real Estate: Therapy - Lake, Laundry, Love it

Sherwood Forest

$262 nightly

Jun 7 - Jun 8

Total with taxes and fees

Cozy Home in Holyoke with 3 bedrooms

Holyoke

Jennifer S.

$334 nightly

Jun 9 - Jun 10

Total with taxes and fees

View all properties

Find vacation rentals that suit your style

Private vacation homes

Aparthotels

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Chester Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"Wonderful hidden gem of a little hotel. Right on lake laurel we had a beautiful lake view. Rooms were very clean. Decent breakfast. Well Located and close to Lee downtown main st, the Lennox Main Street and Stockbridge as well. Looking forward to returning"

Berkshires Untold

8/10 Good

"Here’s what we liked: If we were just reviewing BERKSHIRES UNTOLD based on the staff, we’d be giving it a 5. The staff were extremely friendly, helpful and gracious. When we asked for extra towels and requested a room change, they accommodated those requests immediately. After we switched rooms they checked to see if we were happier. This is exactly the kind of service you want in a hotel or inn. Other good things - The bed was comfortable and there was enough counter space in the bathroom and at the desk area. We also liked that there was a breakfast seating area, bar and small indoor seating area plus outdoor seating with gas fire pits. So, why are we giving the place a 3 overall? It really needed more attention to detail. The carpet in our original room was not in good shape and the fitted bed sheet had a small rip on my side. Some of the room furniture was dinged up and a sofa in the common seating area had some shredded fabric. One thing we didn’t like (that they couldn’t exactly help) was that we were there on a late spring wedding weekend, so there were buses idling in front of our room with loud talkers and smokers nearby. It felt like they were in our room along with the smoke and fumes. The trend of turning motels into better motels is interesting. They’re less expensive and are sometimes more original. But you’re still in a motel. If you value soundproofing and consistently better quality, a mid range chain may be a better choice."

Berkshire Mountain Lodge

10/10 Excellent

"We love the Bershire Mountain Lodge. We've stayed here five other times but this time we do have a few very minor negatives. 1) The cabinet door under the kitchenette sink had a loose hinge. We messaged the staff and requested that they wait until after we checked out to repair the hinge. We hope the hinge was repaired before the next guest checked in. 2) The toilet flush handle was slightly cracked but still functional. We forgot to notify the staff; it was barely noticeable. 3) The guest or owner in the room above our room walked very loudly. We were used to hearing noises from people walking in the hall but this was our first time hearing footsteps through the ceiling. Other than those three items, our stay was excellent. The front desk staff were courteous and helpful. The housekeeping crew were unobtrusive. The long driveway to the ample parking lot gives enough distance from the busy"

Candlewood Suites West Springfield by IHG

8/10 Good

"After my stay at that hotel in Northampton, this was a welcome change. I didn't feel weird about how clean the bed really was before I got in it. Everything was clean. The staff was friendly and helpful. (And it was cheaper!) It's conveniently located to lots of restaurants, fast food and shopping. True, it's a 15 minute drive from Northampton, but my next trip out to Noho, I'll stay here."

Quality Inn & Suites Northampton - Amherst

2/10 Terrible

"I have never stayed in a hotel room so dirty. When I walked in, there was a solid layer of dust, salt(??) and food crumbsw on top of the fridge. I don't know. Maybe they have really short cleaning staff. I went to the local CVS and got a swiffer, spray cleaner and paper towels to clean up. It icked me out from the start. You could see the room was not well dusted or vacuumed. Breakfast? They had the same bagels out for breakfast 4 days runnning. (Day 1 - 12 bagels, Day 2 - 8 bagels.., and so on). After 3 days I went and bought myself a bag of bagels at Trader Joes. I travel a lot. Sometimes I stay in bargin hotels; sometimes nice ones. This was the worst hotel I've stayed at. The staff was pleasant enough, but someone's not doing their jobs there. Never again"

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 $302 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.

Frequently asked questions

Can I find a vacation rental in Chester?

Yes, you can find vacation rentals close to well known sights in Chester, or you can select a more secluded option if you want a relaxing place to stay. Chester is known for its waterfalls and shopping. Make sure you have time to check out the riverfront and restaurants during your trip.

What are some of the best vacation rentals that Chester has to offer?

Cozy Riverside Berkshires Retreat: You might want to consider this vacation home rental near Chester, which is located on a river and has a fireplace, a garden, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and kitchenware, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

What can I see and do in Chester?

While exploring the area, visit family-friendly sights like The Bookstore, or get outside and enjoy nature at Glendale Falls. Chester Town Hall and Pyramid Lake are a couple of places you'll find in the larger area.

What are vacation rentals like in Chester?

Vacation rentals are privately owned accommodations you can book for a short or long stay in Chester. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from shared hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for a family trip.

Room 1

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Chester vacation rentals

Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke

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

Nurse-Ready Studio Retreat! 2 Mi to Dtwn Holyoke

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

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

Peaceful Meadow Retreat

Real Estate: Therapy - Lake, Laundry, Love it

Cozy Home in Holyoke with 3 bedrooms

stylish Berkshires Retreat

Big farmhouse in the foothills of the Berkshires

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Cozy Riverside Berkshires Retreat

Cozy First Floor Apartment. Located in a quiet neighborhood.

Charming Chicopee Getaway

Townhouse with Pool Table - Renovated w/ King Bed

Cozy 2-bedroom apartment in Chicopee

Button's Modern Luxury Walkup Downtown Northampton

Treetop Hideaway in Tyringham

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Find vacation rentals that suit your style

Top Chester Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Berkshires Untold

La Quinta Inn & Suites by Wyndham Springfield MA

Berkshire Mountain Lodge

D. Hotel Suites & Spa

Candlewood Suites West Springfield by IHG

Quality Inn & Suites Northampton - Amherst

Tru by Hilton Chicopee Springfield

Hampton Inn & Suites Berkshires-Lenox

Find out more about Chester

Frequently asked questions

Go further with the Expedia app