Chester Holiday Rentals from €162: Search Short-Term Rentals

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Our top choices for Chester holiday rentals

1. Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy

Epsom

Anthony

includes taxes & fees

16 Nov - 17 Nov

A two-story house with a front porch, surrounded by a well-maintained lawn and trees.

2. Private Studio/Bathroom Handicap Accessible Room in Single Family Home

Windham

includes taxes & fees

19 Oct - 20 Oct

A small, rustic room with a single bed, a cabinet, and a shelf with various items.

3. This one room camping cabin is a great alternative to a tent camp site.

Epping

includes taxes & fees

30 Oct - 31 Oct

A living room with a fireplace, a ceiling fan, a bookshelf, and a coffee bar.

4. Charming & Historic 2BR Oasis in Downtown Luxury

Downtown Manchester

Tracy S.

A neatly made bed with a white duvet and several pillows, a grey rug, and a dark headboard in a room with a simple, clean design.

5. Mini cozy quiet apartment

Rimmon Heights

John B.

includes taxes & fees

16 Nov - 17 Nov

A room with a chandelier, a fireplace, a dining table, a sofa, and a chessboard.

6. The Amoskeag - Ash Street Inn

Corey Square

includes taxes & fees

16 Nov - 17 Nov

A spacious living room with a white sofa, a coffee table, and a chandelier.

7. Marvelous 3-bedroom townhome with Heated floor Manchester

Highlands

Kimberly D.

includes taxes & fees

19 Oct - 20 Oct

A modern kitchen with a central island, bar stools, hanging pendant lights, and a stainless steel refrigerator.

8. Serene Pondside Retreat Surrounded by Nature

Deerfield

Bobbi S.

includes taxes & fees

26 Oct - 27 Oct

A kitchen with wooden cabinets, a dining table, chairs, a ceiling fan, and a view through a glass door.

9. Riverfront 2BR | Home King Suite | Patio & Grill

Epping

Kimberly W.

A stainless steel refrigerator with a water dispenser, wooden cabinets, a granite countertop, and a black trash can.

10. Charming quiet

Rimmon Heights

Sierra M.

includes taxes & fees

16 Nov - 17 Nov

A living room with a wooden floor, a grey sofa, a coffee table with a vase, and a flat-screen TV mounted on the wall.

11. Family Oasis

Kalivas Union

Douglas

includes taxes & fees

15 Nov - 16 Nov

A living room with a brown leather sofa, a wooden coffee table, and a white door.

12. Relaxing Family friendly Apartment!!

Rimmon Heights

Sarah W.

includes taxes & fees

16 Nov - 17 Nov

A living room with a sofa, armchair, coffee table, lamp, and potted plant.

13. Bright & Cozy Entire Apartment - Your New England Hub

Haverhill

Lorraine B.

includes taxes & fees

19 Oct - 20 Oct

A living room with a flat-screen TV mounted on the wall, a dark wooden coffee table with a potted plant and decorative items, and a small side table with a lamp.

14. Heated Winter Stay • 3BR Home • Pet-Friendly • Free Parking • Near Hospitals • 6

Manchester

includes taxes & fees

27 Oct - 28 Oct

A motel with a two-story structure, multiple rooms, and a covered front porch.

15. 1 Full Bed | ADA/RI Shower

Nashua

includes taxes & fees

1 Nov - 2 Nov

A kitchen with white cabinets, a granite countertop, a stove, a sink, and a refrigerator.

16. Lovely Downtown Oasis ~ Hospitals/Colleges/Beaches

Amesbury

Nancy M.

includes taxes & fees

19 Oct - 20 Oct

A modern bedroom with a bed, a TV, a ceiling fan, and a window with blinds.

17. Aariz Nest

Methuen

"Friendly and helpful hostess greeted me upon arrival. VRBO app was very useful for communication. Having a washer and dryer in the unit was great. The TV had Netflix, but I mostly screen casted from my iPad while was there (16 days). Had my own entrance and parking spot in the driveway. I really can't think of any negative outside of a broken handle on the microwave, which was no big deal. Recommended!"

Mark S.

includes taxes & fees

18 Oct - 19 Oct

A modern kitchen with white cabinets, stainless steel appliances, a wooden ceiling, and a green accent wall.

18. Large 3 floor Townhome with Patio, Backyard and Sauna

Rimmon Heights

Kayla B.

includes taxes & fees

19 Oct - 20 Oct

A bedroom with a bed, two bedside tables, a door, and curtains.

19. Downtown Amesbury! 15 Mins to Beach

Amesbury

Holly B.

includes taxes & fees

19 Oct - 20 Oct

A two-story red house with a front porch, a driveway, and a well-maintained garden with various shrubs and a circular lawn feature.

20. Spacious 2BR Apartment Near Bradford & Merrimack Valley Parking Included.

Haverhill

Andrew G.

includes taxes & fees

26 Oct - 27 Oct

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Top Chester Hotel Reviews

Motel 6 Nashua, NH - South

10/10 Excellent

"best motel ive stayed at honestly. Despite the noise & ppl. It was clean"

Exeter Inn

10/10 Excellent

"We enjoyed our stay immensely. It was nostalgic, but clean, cozy and inviting. Breakfast , included, was good, and some mornings great. Staff was all pleasant and helpful. Can't wait until next year. Hope the remodel does not remove the vintage New England vibe because that's what most ppl visiting New England are looking for. Beautiful place. Quiet stay aside from neighbors door slamming shut multiple times a day. Not a deal breaker. Location is good."

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, apart-hotels, 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 €162 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.

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

Indoor Pool, 2 Miles From Ocean, 7,000 Square Foot Luxury Home: This holiday home rental outside of Chester is located in a rural location, and has an indoor pool, a patio and a BBQ to put you at ease in your new surroundings. It has 9 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

What can I see and do in Chester?

While exploring the area, visit family-friendly sights like Canobie Lake Park, or get outside and enjoy nature at Onway Lake. While here, Chester Public Library and Chester Town Hall are other places worth a visit.

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 offer extras such as hot tubs, fire pits and patios so you'll have a home away from home. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for a small group gathering.

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Check prices for these dates

Our top choices for Chester holiday rentals

1. Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy

2. Private Studio/Bathroom Handicap Accessible Room in Single Family Home

3. This one room camping cabin is a great alternative to a tent camp site.