Chester Holiday Rentals from NZ$196: Search Short-Term Rentals

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

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

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In two weeks

In two months

In three months

In four months

Our top choices for Chester holiday rentals

A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

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

Sherwood Forest

Sharon K.

includes taxes & fees

28 Sept - 29 Sept

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

2. Berkshire Mountain Lodge

Pittsfield

Robert

includes taxes & fees

18 Oct - 19 Oct

A hot tub with a string of lights above it, set against a dark night sky.

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

Sherwood Forest

Frank M.

includes taxes & fees

29 Sept - 30 Sept

A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

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

Sherwood Forest

William C B.

includes taxes & fees

5 Oct - 6 Oct

A deck with outdoor furniture, including a sofa and a glass table, overlooking a body of water.

5. Cozy Cottage-Sunset On The Lake

Otis

Rose Angela M.

includes taxes & fees

23 Oct - 24 Oct

A rural property with a wooden barn, a white fence, and a mobile home.

6. Cozy Camper tucked into the woods

Sandisfield

"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.

includes taxes & fees

28 Sept - 29 Sept

A lakeside picnic area with a bench and umbrella, surrounded by autumn-colored trees.

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

Hinsdale

Kyle R.

includes taxes & fees

27 Sept - 28 Sept

A cozy room with two beds, large windows, and a view of a snowy landscape.

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

Easthampton Ma.

Paula

includes taxes & fees

29 Sept - 30 Sept

A house with a porch, a garden with pink flowers, and a stone wall along the road.

9. Big farmhouse in the foothills of the Berkshires

Russell

Will G.

includes taxes & fees

6 Oct - 7 Oct

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

10. Modern Studio Ideal for Traveling Professionals

Holyoke

includes taxes & fees

29 Sept - 30 Sept

A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

11. Treetop Hideaway in Tyringham

Monterey

"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "

Samantha G.

includes taxes & fees

27 Oct - 28 Oct

12. Modern Studio Ideal for Traveling Professionals

Holyoke

Todd J.

includes taxes & fees

29 Sept - 30 Sept

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

Holyoke

Jeremy R.

includes taxes & fees

29 Sept - 30 Sept

A red barn with a black door and a heart-shaped cutout, surrounded by lush greenery and trees.

14. Charming, updated 3 bedroom farmhouse farm stay.

Williamsburg

Nancy M.

includes taxes & fees

27 Sept - 28 Sept

A living room with a fireplace, a sofa, a coffee table, and a TV.

15. Cozy 2-bedroom apartment in Chicopee

Chicopee

Christopher P.

includes taxes & fees

28 Sept - 29 Sept

A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

16. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

Dalton

Allie T.

includes taxes & fees

8 Oct - 9 Oct

A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

17. Riverside Retreat in the Berkshires

Great Barrington

Kelly B.

includes taxes & fees

27 Sept - 28 Sept

A bedroom with a bed, curtains, a bedside table, and a lamp.

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

Chicopee

Nicholas B.

includes taxes & fees

28 Sept - 29 Sept

A living room with a sofa set, a coffee table, and two lamps.

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

Chicopee

Morrris

includes taxes & fees

4 Oct - 5 Oct

A spacious kitchen with a large island, wooden beams, and pendant lighting.

20. Linny's - Private Dock - Lake Access - Firepit

West Suffield

Wendy C.

includes taxes & fees

14 Oct - 15 Oct

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Top Chester Hotel Reviews

Hotel On North

10/10 Excellent

"We enjoyed our stay. A unique property. This was a quick overnight to attend a show at tanglewood. Dined at the restaurant on the property, which was convenient and very good as well. Would visit again."

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good

"It’s an older facility , as expected, but with great character and very clean . Special praise goes to the staff , in particular , Michele at the front desk . Super nice and very helpful in answering our questions about the local activities . Will keep in mind for another visit ."

Holiday Inn Club Vacations Oak 'n Spruce Resort

8/10 Good

"I stayed in a townhouse, an upgrade from the room I booked. It was quiet and private, which I enjoyed, and more room than I needed. If my family's schedule had been different, I could have invited them over for a cookout (they live nearby). The townhouse was rather dated and I am afraid a bit dreary, with a lot of browns and beiges. But well-outfitted and convenient."

Find out more about Chester

Everything you need to know about Chester 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 Chester 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 Chester holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chester holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chester 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 Chester holiday rentals we have selected for you start as low as NZ$196 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester 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 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 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 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 holiday rental in Chester?

Yes, there are holiday rentals close to the most popular sights in Chester, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Chester has to offer?

Experience Three Sisters Sanctuary in Goshen, MA: This holiday home rental outside of Chester 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 Chester?

While exploring the area, visit family-friendly sights like Bousquet Ski Area, or get outside and enjoy nature at Pyramid Lake. Chester Town Hall and Blandford Ski Area are a couple of places you'll find in the wider area.

What are holiday rentals like in Chester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chester. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for family gatherings.

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Check prices for these dates

Our top choices for Chester holiday rentals

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

2. Berkshire Mountain Lodge

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

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

5. Cozy Cottage-Sunset On The Lake

6. Cozy Camper tucked into the woods

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

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

9. Big farmhouse in the foothills of the Berkshires

10. Modern Studio Ideal for Traveling Professionals

11. Treetop Hideaway in Tyringham

12. Modern Studio Ideal for Traveling Professionals

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

14. Charming, updated 3 bedroom farmhouse farm stay.

15. Cozy 2-bedroom apartment in Chicopee

16. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

17. Riverside Retreat in the Berkshires

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

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

20. Linny's - Private Dock - Lake Access - Firepit

Find holiday rentals that suit your style

Top Chester Hotel Reviews

Hotel On North

La Quinta Inn & Suites by Wyndham Springfield MA

Quality Inn West Springfield

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Hotel Northampton

Berkshires Untold

Holiday Inn Club Vacations Oak 'n Spruce Resort

The Red Lion Inn

The Whitlock

Find out more about Chester

Frequently asked questions

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