Chester Vacation Home Rentals from CA $387: Search Top Private Vacation Homes for Rent

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Our top choices for Chester vacation homes

1 bedroom, desk, iron/ironing board, travel crib

The Creation Station is a cozy place so make yourself at home.

Easthampton Ma.

Christopher K.

CA $387 total

includes taxes & fees

May 28 - May 29

3 bedrooms, desk, iron/ironing board, travel crib

Townhouse with Pool Table - Renovated w/ King Bed

Chicopee

RAFAEL U.

CA $616 total

includes taxes & fees

Jun 1 - Jun 2

Cozy Home in Holyoke with 3 bedrooms

Holyoke

Jennifer S.

CA $517 total

includes taxes & fees

Jun 1 - Jun 2

Big farmhouse in the foothills of the Berkshires

Russell

Amanda C.

CA $481 total

includes taxes & fees

May 27 - May 28

Cozy cottage in the Berkshires

PITTSFIELD

CA $505 total

includes taxes & fees

May 29 - May 30

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Sherwood Forest

Frank M.

CA $541 total

includes taxes & fees

Jun 2 - Jun 3

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Sherwood Forest

Sharon K.

CA $516 total

includes taxes & fees

Jun 2 - Jun 3

Real Estate: Therapy - Lake, Laundry, Love it

Sherwood Forest

CA $459 total

includes taxes & fees

Jun 10 - Jun 11

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Top Chester Hotel Reviews

Berkshire Mountain Lodge

10/10 Excellent

"Clean room. Very well equipped. It is a hidden gem, close to everything. Great experience"

Baldwin Inn & Suites, SureStay Collection by Best Western

4/10 Poor

"The staff were all decent people but the sheets were like sleeping on plastic. The Buffett breakfast consisted of literally just toast because they were out of everything. The shades in my room were awful. Lastly, the entire hotel smelled like cigarettes and the people staying there were sketchy as hell."

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent

"The rooms are not at all fancy, but perfect for a family if you want to get away for a few nights. We went with my 3, 4, and 7-year-olds and spent two nights playing in the pool, mini-golfing, and hitting the arcade once or twice. Again, not very high-end, but if you’re with children who love a pool and easy activities, it’s a good choice."

La Quinta Inn & Suites by Wyndham Springfield MA

6/10 Okay

"El.primer cuarto que nos dieron olía a humo de cigarrillo cuando el hotel dice que es de no fumadores pero la muchacha que nos atendió muy hamable nos cambió rapido de habitación. La piscina estaba bn pero creo creo q le le hace falta mantenimiento y mas luz para el disfrute"

Quality Inn & Suites Northampton - Amherst

6/10 Okay

"The Room was basic. It had a desk chair and a bed. I would have liked a comfortable chair for watching TV and reading. I had to call for a luggage stand as there was none in the room. Breakfast was minimal and I had to find an attendant to replenish several items. The only cold cereals was heavily sugared, perhaps aimed at children. The "hot" water for tea was only lukewarm. Upon checkout I had to leave my keys at an unattended desk. That about sums up the experience. The only outstanding experience was check-in which was very friendly and helpful."

Find out more about Chester

Chester Vacation Homes information

Number of reviews	336
Accommodation	263 Vacation Homes
Lowest Price	CA $387
Highest Price	CA $1,189

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chester vacation homes

The Creation Station is a cozy place so make yourself at home.