Sheffield, MA, USA Vacation rentals • comparison for Airbnb, Vrbo and Booking prices

United States Massachusetts Great Barrington vacation rental compare prices direct by owner 33520594

Idyllic Retreat; Hot Tub/Sauna by Evergreen Home

5.0 (42)

3 Bedrooms • 8 Guests

$838 avg/night

United States New York Copake vacation rental compare prices direct by owner 36062204

Valley View: Renovated Cottage, New Addon + Pool

5.0 (32)

5 Bedrooms • 10 Guests

$1,396 avg/night

United States Massachusetts Great Barrington vacation rental compare prices direct by owner 13095826

River Cottage: Riverfront Home, Walkable Community

5.0 (109)

3 Bedrooms • 6 Guests

$779 avg/night

United States Massachusetts Sheffield vacation rental compare prices direct by owner 3574735

Little House in the Woods by Evergreen Home

5.0 (111)

2 Bedrooms • 6 Guests

$434 avg/night

United States Massachusetts Great Barrington vacation rental compare prices direct by owner 25055050

Renovated Private Guest House by Evergreen Home

5.0 (27)

2 Bedrooms • 5 Guests

$152 avg/night

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United States New York Ghent vacation rental compare prices direct by owner 27827009

Grand Estate w/ Mountain Views by Evergreen Home

4.9 (59)

7 Bedrooms • 12 Guests

$982 avg/night

United States New York Town of Hillsdale vacation rental compare prices direct by owner 9856795

Silver Ridge: Hilltop Chalet w/ Sweeping Views

4.9 (34)

4 Bedrooms • 8 Guests

$949 avg/night

United States New York Pine Plains vacation rental compare prices direct by owner 28582834

Tanner Farmhouse - Rural Cozy Escape

4.8 (33)

3 Bedrooms • 6 Guests

$547 avg/night

United States Massachusetts New Marlborough vacation rental compare prices direct by owner 23635940

Meadow Top Cottage: Countryside Cottage on 72 Acre

4.8 (32)

3 Bedrooms • 6 Guests

$477 avg/night

United States New York Town of Hillsdale vacation rental compare prices direct by owner 28122754

Olive Pit: Scenic Designer Retreat +Pool—Sleeps 12

4.7 (17)

5 Bedrooms • 12 Guests

Available on

United States Connecticut Canaan vacation rental compare prices direct by owner 33526093

Music Mtn Farmhouse - Mystical Country Retreat

4.5 (2)

4 Bedrooms • 8 Guests

Available on

United States Massachusetts Great Barrington vacation rental compare prices direct by owner 25600029

Chic, Mid Century, on The Hill, in GB!

5.0 (15)

3 Bedrooms • 8 Guests

$605 avg/night

United States Massachusetts Great Barrington vacation rental compare prices direct by owner 28227297

Hot Tub, Wood Stove, Fenced Yard: Sleeps 8+

5.0 (25)

4 Bedrooms • 10 Guests

$775 avg/night

United States Massachusetts Egremont vacation rental compare prices direct by owner 32736132

Stylish, Spotless, Ping-Pong, Gas Fireplace!

5.0 (23)

5 Bedrooms • 12 Guests

$847 avg/night

United States Massachusetts Great Barrington vacation rental compare prices direct by owner 37345742

Huge screen porch, Chef's Kitchen l Prime Location

5.0 (5)

4 Bedrooms • 10 Guests

$794 avg/night

United States Massachusetts Egremont vacation rental compare prices direct by owner 2641386

Cozy Lake Cottage, Fireplace, Close to Catamount!

5.0 (49)

3 Bedrooms • 6 Guests

$453 avg/night

United States Massachusetts Great Barrington vacation rental compare prices direct by owner 25732137

Luxury Redo: Hot Tub, Playroom, Sleeps 12

5.0 (45)

5 Bedrooms • 12 Guests

$955 avg/night

United States Massachusetts New Marlborough vacation rental compare prices direct by owner 24109993

Ski Rental: Game Room, Hot tub, Sauna, Fireplaces!

5.0 (31)

5 Bedrooms • 14 Guests

$1,359 avg/night

United States Massachusetts Great Barrington vacation rental compare prices direct by owner 9676490

5 Stars w/ Hot Tub, Sunny Patio, Game Room, Views!

5.0 (24)

4 Bedrooms • 14 Guests

$1,007 avg/night

United States Massachusetts Monterey vacation rental compare prices direct by owner 2095068

Cozy, Lake Views, Ski Weekends, Sleeps 8!

5.0 (22)

3 Bedrooms • 8 Guests

$603 avg/night

United States Connecticut Norfolk vacation rental compare prices direct by owner 27212723

The Cottage at Blackberry River Inn

5.0 (19)

1 Bedroom • 2 Guests

$358 avg/night

United States Massachusetts Great Barrington vacation rental compare prices direct by owner 2823058

Winter Lake Views, Close to Butternut!

4.9 (31)

4 Bedrooms • 8 Guests

$644 avg/night

United States Massachusetts Great Barrington vacation rental compare prices direct by owner 11160413

Sunsets, Fireplace, 5 mins to Butternut, Sleeps 8!

4.9 (33)

4 Bedrooms • 8 Guests

$936 avg/night

United States Massachusetts Stockbridge vacation rental compare prices direct by owner 4832753

Hot tub, Cozy, Wood Stove, Ski Holidays!

4.9 (13)

4 Bedrooms • 7 Guests

Available on

United States Massachusetts Egremont vacation rental compare prices direct by owner 23667719

Hillside Haven: Modern near Great Barrington

4.9 (44)

1 Bedroom • 10 Guests

$850 avg/night

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