Holiday houses in Chester

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Top-rated holiday rentals in Chester

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Superhost

Cottage in Windham

4.91 out of 5 average rating, 85 reviews

Tranquil waterfront cottage

Jo-AnnRating, 5 stars7 months ago

This Lakeside Retreat was a perfect weekend escape for two couples. In late September, we seemed to have the pond to ourselves and enjoyed sharing time around the firepit overlooking the lake. The Bathroom was spacious and one level up from the bedrooms downstairs. The kitchen had everything needed to prepare an excellent meal. I would highly recommend this cabin to a a small group of friends or family looking for a great location near Portland and Lake area attractions.Our host Bobbi was very responsive.

Top Guest favourite

Apartment in Arundel

4.98 out of 5 average rating, 330 reviews

Cape Arundel Cottage 1 mile to downtown KPT

WarrenRating, 5 stars1 month ago

Hillary's place was a wonderful place to stay for a cozy weekend getaway. It felt very homey with personal touches. We were here during a little snowstorm so we didn't spend any time outside but the yard and private deck were really nice. We had some troubles with the hot water but Hillary was very responsive and helpful! We would definitely stay here again.

Top Guest favourite

Home in Windham

4.94 out of 5 average rating, 129 reviews

Waterfront Gem walkable to Restaurants!

RachaelRating, 5 stars1 week ago

Beautiful house on the pond! Perfect for our family of 4. It was comfortable and relaxing. Amy is a wonderful host! She checked in and made sure we had everything we needed. We really enjoyed our stay! Hoping to stay again sometime.

Superhost

Home in Wells

5 out of 5 average rating, 3 reviews

"In Tempore" Cottage

AllisonRating, 5 stars9 months ago

Gisele and her property manager were promptly responsive. The cottage was extremely clean, newly decorated and well appointed. The layout was very comfortable for our family of four. The pools were nice and not overly crowded. The only negatives were: If not taking the trolley or golf cart, the closest pool was a half mile walk with no parking available. The further pool did have parking. Also, no outside water source/hose to rinse off. Plenty of restaurant choices nearby in Wells, Ogunquit and Kennebunkport. Wells beaches were beautiful with easy, affordable parking. Overall a wonderful stay in Wells!

Guest favourite

Home in Harrisville

4.9 out of 5 average rating, 10 reviews

Harrisville Lake House - A Tranquil Get-Away

JudyRating, 5 stars7 months ago

I’m grateful that Peggy and Harry were willing to rent to us at the last minute. Our family needed a quiet respite to be together during a difficult time of loss. The solitude of the lake and woods was calming and we had plenty of room to be together. I only wish we could have stayed longer!

Superhost

Apartment in Kennebunkport

4.93 out of 5 average rating, 29 reviews

Charming Kennebunkport

EmilyRating, 5 stars8 months ago

My husband and I stayed at Kristen’s apartment for 2 weeks at the end of August and had the most amazing time! This was our 3rd time to KPT and most definitely our favorite thanks to this gorgeous Airbnb and Kristen’s hospitality. The apartment was perfect for us — was exactly as described, better than the photos with amazing windows and views, speedy WiFi perfect for working remotely. It’s a quick 4 minute drive into town, and such a beautiful area to walk around. Kristen was so responsive and helpful — there’s a super extensive list of local reccs in the apartment, and a beach pass that you can use during your stay. We loved this home away from home, and can’t wait to come back soon!

Superhost

Cottage in Hill

4.98 out of 5 average rating, 87 reviews

The red house

MeganRating, 5 stars1 month ago

Great location close to Ragged Mountain for winter sports. Comfortable home, lots of beds for kids (wish the homes we had stayed in when our kids were little were as well stocked with toys and a fun toddler bed!) Also loved that the pantry was stocked-we unexpectedly got to have fresh baked muffins with breakfast.

Guest favourite

Home in Ogunquit

5 out of 5 average rating, 27 reviews

Hoyts Ahoy

KimberlyRating, 5 stars2 days ago

We were a couple plus two singles in town to run the Maine Coast half marathon in Wells, and wanted somewhere to stay together that was also walkable to things. This house was perfect for this purpose! Very clean, comfortable beds, spacious kitchen + living room for hanging out, easy to get to things in Ogunquit (walking) and Wells (driving). Thank you!

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Guest favourite

Home in Scarborough

4.93 out of 5 average rating, 59 reviews

Gorgeous 4 BR home with HOT TUB

ShellyRating, 5 stars2 weeks ago

Gregory's place was great for our 2 night getaway. Hot tub was amazing and private from neighbors. Bathrooms and kitchens were well stocked. I will definitely go back for another getaway

Guest favourite

Home in Hampton

4.9 out of 5 average rating, 79 reviews

Lux Getaway! Perfect for Groups 8+ppl

AhmedRating, 5 stars5 months ago

Josh and Tracy are very nice and friendly and their place is amazing! I highly recommend their place to anyone visiting the area!

Guest favourite

Apartment in Hampton

5 out of 5 average rating, 9 reviews

Beachside Bliss: Hampton North Beach Condo

LindaRating, 5 stars19 months ago

Great place that’s got everything you need. Just like advertised. Nice and safe area, very close proximity to the beach. Joe is a great host, very responsive and will make sure you feel right at home.

Guest favourite

Home in Freedom

4.9 out of 5 average rating, 94 reviews

Our Mountain Retreat – Lake Ossipee Access

FinRating, 5 stars1 month ago

Paula’s was the perfect spot for a weekend trip with a group of friends for my birthday! It had plenty of sleeping spots for us and was very comfortable, and we really loved the hot tub. They were such responsive and communicative hosts as well, and offered us a flexible late check-out. Thank you!

Guest favourite

Home in Enfield

4.95 out of 5 average rating, 19 reviews

Upper Valley Shaker-Style Home, close to Dartmouth

ScottRating, 5 stars6 months ago

Barbara's place is a real gem. So clean, with a beautiful mix of antique and woodsy modern furniture, and a wonderfully comfortable living area overlooking a meandering brook which a few hundred yards down the road leads to the lake. The kitchen was well-equipped and modern, and beddings and beds were very comfortable. While the house was close too a busy road, we didn't hear a thing, and for summer users the deck is completely away from the road, overlooking the brook. Even more than we expected.

Guest favourite

Home in Holderness

4.9 out of 5 average rating, 10 reviews

Beautiful Home away from Home

StefanieRating, 5 stars2 months ago

My friends and I had a wonderful stay at this house hosted by Byron Property Management. They had snacks waiting for us when we arrived, Christina was kind and quick to respond when we had a question, and the house was exactly what was demonstrated in their advertisement. We are excited to come back next year and hopefully make this an annual trip at this property!

Top Guest favourite

Apartment in Old Orchard Beach

5 out of 5 average rating, 50 reviews

Horizon View Hideaway with Deck

ReneeRating, 5 stars6 months ago

The house is beautiful and very comfortable. We had everything we needed. The host was very friendly and responsive. We would definitely stay there again.

Guest favourite

Home in Old Orchard Beach

4.84 out of 5 average rating, 31 reviews

Beautiful Spacious OOB Beachfront home w/ elevator

AnaRating, 5 stars2 weeks ago

We went off season and it was a very beautiful and tranquil beach experience. The house is gorgeous and spacious. Jason was very responsive and friendly. We will definitely be back!

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