Holiday Rentals in Chester

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Check prices for these dates

Holiday Rentals in Chester

Postcard Cabins Blake Brook

2.0 star property
9.6 out of 10, Exceptional, (4)
"Amamos a experiência,local limpo e aconchegante "
The price is €94
includes taxes & fees
3 Mar - 4 Mar
Postcard Cabins Blake Brook

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

9.4 out of 10, Exceptional, (83)
"We had our annual friends weekend away & Chelsi’s house was the perfect setting for it all! So spacious, there was a room for everyone to do just what they wanted! Pool, hot tub & sauna was a fun added bonus! The theater room was great for the guys who wanted to hang there! Kitchen was really well stocked & had so much room for us all to gather. Beds were comfy & all the linens were cozy too! We had a great time & hope to come back! Thanks Chelsi!"
The price is €2,271
includes taxes & fees
17 Feb - 18 Feb
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

Charming 1825 Farmhouse Near Boston & Canobie Lake

9.4 out of 10, Exceptional, (10)
"Really enjoyed our stay for a weekend getaway. The house was very clean and true space was perfect for our family of 6.Upon checking, just note that the entrance door is in the middle of the unit, not by the parking spaces off the left driveway"
The price is €441
includes taxes & fees
18 Feb - 19 Feb
Charming 1825 Farmhouse Near Boston & Canobie Lake

Enchanting Romantic Riverfront Cottage

2.0 star property
10.0 out of 10, Exceptional, (4)
"Great house, in a great location. Lilly is super communicative. We are already planning another stay when we can get out on the river."
The price is €331
includes taxes & fees
16 Feb - 17 Feb
Enchanting Romantic Riverfront Cottage

The House at Harvey Lake

9.4 out of 10, Exceptional, (21)
"The hosts were wonderful! Ample supply of boats and life jackets. Beautiful location!"
The House at Harvey Lake

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

Cozy home with hot tub minutes to downtown Nashua and Shops

9.6 out of 10, Exceptional, (17)
"Perfect stay for our trip!!"
The price is €567
includes taxes & fees
13 Feb - 14 Feb
Cozy home with hot tub minutes to downtown Nashua and Shops

Relaxing family friendly apartment

9.8 out of 10, Exceptional, (8)
"Enjoyed our stay!!!!"
The price is €282
includes taxes & fees
13 Feb - 14 Feb
Relaxing family friendly apartment

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

Cozy Salem Studio Near Tuscan Village & Boston

9.8 out of 10, Exceptional, (18)
"I was delighted with this adorable studio. It had everything I needed. Very comfy and clean. Check in was so easy and property manager was very responsive. I’ll be back! "
Cozy Salem Studio Near Tuscan Village & Boston

Across From Tuscan Family Farmhouse

9.6 out of 10, Exceptional, (4)
"The host was very communicative up to the day we checked in. Anytime there was a question I had the response was quick. The house was equipped with everyday necessities even laundry detergent which was very nice. I feel like everything was very considerate. The house was very lovely and it was in a great location. "
The price is €1,470
includes taxes & fees
23 Feb - 24 Feb
Across From Tuscan Family Farmhouse

North End Family Oasis

9.6 out of 10, Exceptional, (14)
"It is an entire house, so a good amount of space. Brand new remodel (we were there in Jan 2025). The kitchen/family room is great for meals and hanging out. The bedrooms and bathrooms are wonderful. The photos show how nice. There is even a deck out back. We had 8 adult family members and could have easily fit a few more. And only 1 mile to downtown Manchester. "
North End Family Oasis

Trendy Downtown Nashua Getaway: Checkers-Themed 1 Bed/1 Bath!

2.0 star property
6.0 out of 10, (3)
"The host was very friendly, helpful and prompt when I needed help and had questions. Thank you. "
Trendy Downtown Nashua Getaway: Checkers-Themed 1 Bed/1 Bath!

Charming 4-bedroom unit with 2 full bathrooms in serene Methuen Ma

10.0 out of 10, Exceptional, (1)
"Lovely home and FANTASTIC customer service. Quick response for any requests. I asked about a coffee pot and he brought a brand new pot. It snowed and without being asked he came and shoveled and salted the walk and driveway. I will happily visit again. "
Charming 4-bedroom unit with 2 full bathrooms in serene Methuen Ma

Maple Place Private Guest House

10.0 out of 10, Exceptional, (3)
"This apartment was exactly as advertised - spotless, beautifully furnished, quiet neighborhood, fully stocked with all necessities. The hosts, Tammy and Marc, were very responsive to our needs. It was a perfect place to call home for three weeks."
Maple Place Private Guest House

A spacious modern elegant 3 bedroom Ranch, Whole House located in South Nashua.

9.4 out of 10, Exceptional, (6)
"It was as described on their website. Large ranch. Plenty of room. Comfortable beds and furniture. Kitchen has everything. Outside grill and firepit. Large fenced in yard. Contacted host MANY times during our stay with multiple questions. Always returned my texts quickly. Nothing major. Just things I couldn't find or how Ishould do something. I always received an answer within 10-15 minutes"
A spacious modern elegant 3 bedroom Ranch, Whole House located in South Nashua.

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 €293
includes taxes & fees
13 Feb - 14 Feb
Pet friendly, quiet home away from 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

Baboosic Lake - Wonderful Classic S. NH Vacation Cottage all to Yourself

9.6 out of 10, Exceptional, (18)
"Our kids said the beds were the most comfortable beds they'd ever slept on, with the coziest blankets. The cabin was warm, cozy, and homey. Host was very nice and communication was timely and helpful. Beautiful view on the lake. Close to all amenities, shopping, and grocery stores."
Baboosic Lake - Wonderful Classic S. NH Vacation Cottage all to Yourself
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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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, (1002)
"Great"
The price is €120
includes taxes & fees
20 Feb - 21 Feb
DoubleTree by Hilton Manchester Downtown

Park View Inn - Salem

2.0 star property
8.8 out of 10, Excellent, (1242)
"Excellent place to stay with dedicated and polite staff"
The price is €89
includes taxes & fees
13 Feb - 14 Feb
Park View Inn - Salem

Country Inn & Suites by Radisson, Manchester Airport, NH

3.0 star property
8.0 out of 10, Very good, (1224)
"In the presitr of reavatipn but it was still good"
The price is €104
includes taxes & fees
23 Feb - 24 Feb
Country Inn & Suites by Radisson, Manchester Airport, NH
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. Chester Village Cemetery and Zorvino Vineyards 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 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.