Chester Holiday Rentals
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48 rentals in Chester.
Cozy Berkshires Vacation Rental Near Hiking!
Condo/Apartment
4 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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NEW! Sunday Farm - 1840's Whaling Captain's Estate
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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The following properties within 20 miles of Chester match all your filters:
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
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Peace and quiet on the lake
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A-Frame in Sherwood Forest
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Charming cedar shingle cottage
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Pristine Home In Becket Woods
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HavenHaus: Cozy A-Frame Cabin in the Berkshires
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Charming Farmhouse - quiet, private & peaceful
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Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.
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East Otis, MA, Waterfront Summer Cottage, Big Pond,
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East Otis, MA, Waterfront Summer Cottage, Big Pond,
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Beautiful Timber Frame Home in the Berkshires /Available for Long Term
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Two Bedroom house in the heart of the Berkshires
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Lakefront Cottage In The Berkshires In Western Massachusetts
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A-Frame Cabin w/ Furnished Deck in Becket!
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Home in The Berkshires - Becket
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Berkshires Cabin Steps to Lake
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Berkshires Retreat W/ Sauna by Evergreen Home
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Private Cabin On Over 12 Acres Of Woods!
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Historic Huntington Home - Walk to Westfield River
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Little Longbow Lakefront Chalet
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Lake, Tennis, Beach Access, Skiing, Kayaking, Fishing
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tranquil 3-BR Waterfront Retreat
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New Listing Contemporary Cottage in the Woods viewing a Private Spring Fed Pond
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Becket Contemporary Cottage in the Woods Overlooking a Private Spring Fed Pond
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Beautiful four season lakeside log home close to all Berkshires attractions.
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Hip Renovated Mid Century 4 Bedroom on Long Bow Lake
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Berkshires Home on 11 Acres w/ Pond & 2 Fire Pits!
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Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow
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Wildlife Retreat in the Forest
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Beautiful Spacious Berkshire A-Frame Mountain House
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Quintessential 1860's Berkshire farmhouse with mountain views on 30 acres.
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Spacious waterfront Berkshire home family private get-away
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Sprawling Berkshires Ranch Nestled In A Private Wooded Lot With Expansive Yards!
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Lake House In The Heart Of The Berkshires
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Berkshires Lakefront Retreat
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Lakeside 3-BR Berkshires Residence
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Fall Berkshires Retreat! Dog friendly, Hot Tub, Hiking, Canoe!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Hilltown Nest is a wonderful place for family and friends to gather.
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Becket Home w/ 3-Season Porch: Walk to Lake Access
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Lakeside 5-BR Home in Idyllic Berkshires
Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Private Lakehouse in the heart of the Berkshires
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Shingle style, Timber Frame, Berkshire Cottage beside babbling brook
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Lakefront Jewel By: Evergreen Home
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Private Lake Cottage on 3 acres w/350 sq. ft. deck
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Quintessential 6-BR Berkshires Lodge
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Serene 3-BR Berkshires Log Cabin
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Showing results 1-48 of 48
Frequently Asked Questions about Chester
- Yes, here are some popular holiday rentals in Chester that have a pool:
- Cozy Berkshires Vacation Rental Near Hiking!
- NEW! Sunday Farm - 1840's Whaling Captain's Estate
- Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
- Yes, here are some popular holiday rentals in Chester that have internet access:
- Cozy Berkshires Vacation Rental Near Hiking!
- NEW! Sunday Farm - 1840's Whaling Captain's Estate
- Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
- Some of the most popular kid friendly rentals in Chester are:
- Cozy Berkshires Vacation Rental Near Hiking!
- NEW! Sunday Farm - 1840's Whaling Captain's Estate
- Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
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