Chester Holiday Rentals

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

This weekend
Next weekend

Holiday Rentals in Chester

Postcard Cabins Blake Brook

2.0 star property
9.6 out of 10, Exceptional, (5)
"Amamos a experiência,local limpo e aconchegante "
The price is AU$234
includes taxes & fees
27 Mar - 28 Mar
Postcard Cabins Blake Brook

Indoor Pool, 2 Miles From Ocean, 7,000 Square Foot Luxury Home

9.6 out of 10, Exceptional, (84)
"This is a charming 400-year-old farmhouse that has been well-loved and is perfect for hosting large get togethers. While it has been updated over the years, most of the original layout remains intact. There are lots of rules, but none are unreasonable, and there is a lot to know simply because it is a very large, historic home. This house feels warm and welcoming. It has tons of windows offering lots of light and lovely views from every room. There are six bedrooms upstairs, and the room off the...
The price is AU$3,731
includes taxes & fees
16 Mar - 17 Mar
Indoor Pool, 2 Miles From Ocean, 7,000 Square Foot Luxury Home

Peek-a-Boo Lake Views & Yard: Windham Home

10.0 out of 10, Exceptional, (1)
"We have rented thru VRBO before. This was by far our best experience. The house had everything we needed (no running out first thing for toilet paper) Best of all was the Christmas tree and decorations. It really made it “home for the holiday.”The agent and owners were super communicative, let us know what and where’s promptly.I can’t thank them enough for the experience. Our dog loved the space it trapped in a hotel room."
Peek-a-Boo Lake Views & Yard: Windham Home

Quaint Dunbarton Waterfront Cottage

9.4 out of 10, Exceptional, (46)
"LOVELY AND PEACEFULVERY KIND HOST."
Quaint Dunbarton Waterfront Cottage

Charming 1-bedroom house in Manchester w/ WiFi. Work, school, or business trip?

The price is AU$187
includes taxes & fees
18 Mar - 19 Mar
Charming 1-bedroom house in Manchester w/ WiFi. Work, school, or business trip?

Safe Peaceful Quite Bright Gorgeous Accessibility

The price is AU$648
includes taxes & fees
31 Mar - 1 Apr
Safe Peaceful Quite Bright Gorgeous Accessibility

Relaxing family friendly apartment

9.8 out of 10, Exceptional, (8)
"Enjoyed our stay!!!!"
The price is AU$561
includes taxes & fees
16 Mar - 17 Mar
Relaxing family friendly apartment

Lakefront Salem Retreat - Fish, Swim, Kayak & More

8.8 out of 10, Excellent, (8)
"Overall, we were happy with our stay. We were there in the winter, so we didn't get to enjoy the lake. The house was great as a launch point between Boston and the mountains.The house is literally on the lake. Water touches the lake side of the house. When we were there, the lake was frozen and beautiful.The house was well stocked and perfectly ready for us. There's plenty of parking. It's an older house, so the ceilings can be low and the floors are sometimes uneven. But the main room is...
Lakefront Salem Retreat - Fish, Swim, Kayak & More

Charming quiet apartment

9.8 out of 10, Exceptional, (7)
"Great 3 bedroom home very clean everything you’ll need when your away from home "
The price is AU$516
includes taxes & fees
16 Mar - 17 Mar
Charming quiet apartment

2-bedroom vacation home 30 minutes from Boston and NH beaches

9.4 out of 10, Exceptional, (6)
"My brother and I stayed while we were visiting family. We found the home clean and comfortable with easy access to the highways we needed. It provided a cozy relaxing atmosphere after a day of running. Mary, the host responded quickly to questions and was very easy to work with. All in all, a great stay. Will rent again when I the area. "
2-bedroom vacation home 30 minutes from Boston and NH beaches

Luxurious Spa Suite with Jacuzzi, Outdoor Sauna, Plunge Pool and Steam-bath

10.0 out of 10, Exceptional, (52)
"We had a great time staying here with all of the spa amenities. Massage chair is very nice, hot tub, cold plunge and sauna were a great. King bed was comfy and shower was very nice. Heated bathroom floor is awesome. Host was wonderful and accommodating. Typically we look for more private stays but this was definitely worth the change up. "
Luxurious Spa Suite with Jacuzzi, Outdoor Sauna, Plunge Pool and Steam-bath

Entire House, Sleep 11, Garage, Fully Fenced Backyard

10.0 out of 10, Exceptional, (2)
"Our family of 7 enjoyed the space this house offered. Lei was very quick in responding to questions. The neighborhood was very peaceful and quiet. My kids really enjoyed the Pine St. Eatery for breakfast and it's right around the corner from this house."
Entire House, Sleep 11, Garage, Fully Fenced Backyard

Whispering Pines Retreat Perfect Location

9.6 out of 10, Exceptional, (14)
"The spacious house has a good kitchen and roomy bedrooms. There was plenty of parking space even with the snow and winter weather. "
Whispering Pines Retreat Perfect Location

Triple Family Unit Combined

The price is AU$1,443
includes taxes & fees
9 Mar - 10 Mar
Triple Family Unit Combined

New England Lake Vacation Home

8.8 out of 10, Excellent, (59)
"We had a very nice stay. The improvements in the furniture setup made it much more liveable. Also, the weather was fantastic."
New England Lake Vacation Home

All-Season Cozy Lakeside Cabin in Northwood, NH- 2 Bdr, great views

10.0 out of 10, Exceptional, (26)
"Great location. There are neighbors, but you feel like you are all alone. Perfect for relaxation by the fire. Would definitely go back."
All-Season Cozy Lakeside Cabin in Northwood, NH- 2 Bdr, great views

Pet friendly, quiet home away from home!

9.4 out of 10, Exceptional, (16)
"This property is large, except for the bathroom, with one nice tv, fully stocked kitchen and bathroom and perfect for spending nights. A directory with info such as wifi password would be helpful. Several light bulbs are missing/burned out. "
The price is AU$479
includes taxes & fees
6 Mar - 7 Mar
Pet friendly, quiet home away from home!

Warm house with pool table, large deck, AC, washer/dryer, & beautiful kitchen

6.6 out of 10, (14)
"It had plenty of space for Christmas away"
Warm house with pool table, large deck, AC, washer/dryer, & beautiful kitchen

Waterfront Cottage

9.6 out of 10, Exceptional, (35)
"The property was perfect for what we needed and we will definately be staying again."
Waterfront Cottage

Enchanting Romantic Riverfront Cottage

2.0 star property
10.0 out of 10, Exceptional, (5)
"Came here for a cozy weekend without the kids and it was perfect! We slept in late and woke up to beautiful images of the frozen lake covered in snow. 8 minute drive to downtown and restaurants followed by cozy day reading and watching movies. Everything was clean and well stocked and so convenient. A perfect getaway!"
Enchanting Romantic Riverfront Cottage
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.
Don't see what you're looking for?
See all available properties in Chester
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Chester you may be interested in

DoubleTree by Hilton Manchester Downtown

4.0 star property
9.0 out of 10, Wonderful, (1004)
"The view "
The price is AU$219
includes taxes & fees
23 Mar - 24 Mar
DoubleTree by Hilton Manchester Downtown

Best Western Plus Executive Court Inn & Conference Center

3.0 star property
8.4 out of 10, Very good, (1139)
"Nice room, no problems, staff was courteous "
The price is AU$170
includes taxes & fees
18 Mar - 19 Mar
Best Western Plus Executive Court Inn & Conference Center

Park View Inn - Salem

2.0 star property
8.8 out of 10, Excellent, (1270)
"Very nice staff and really cute room. Highly recommend "
The price is AU$135
includes taxes & fees
18 Mar - 19 Mar
Park View Inn - Salem
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.

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 Lake Massabesic. 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.