The Valley is known for our picturesque red tobacco barns and expansive cornfields.
Front Hallway into house
Entry as you walk in the door
60" Smart TV and Twin Day bed with Trundle
Brand New Kitchen with quartz countertops and all Brand New Stainless Steel appliances. Icemaker and water dispenser in the fridge.

Amherst, Perfect Location, UMass, Smith, MHC!

3 bedrooms·1 bath
Hadley • Massachusetts

$1,475.00 USD total for 3 nights

Oct 20 – 23, 2026

Nestled in scenic surroundings, just a heartbeat away from outdoor adventures
Spacious and vibrant, equipped for family entertainment and relaxation
Fire pit and Adirondack chairs in the yard
Dine al fresco on our spacious patio; perfect for enjoying morning coffee outdoors or evening conversations under the warm glow of our elegantly lit covered porch, a cozy spot for nightcaps
Sleek, modern kitchen equipped with state-of-the-art appliances and a spacious layout for culinary adventures

Berkshires Escape - ski, hike, museums, and more!

4 bedrooms·2 baths
Adams • Massachusetts
4.98(61 reviews)
$200/ night(excl. fees & taxes)
Condo near Mass Moca
Condo near Mass Moca
Condo near Mass Moca
Condo near Mass Moca
Condo near Mass Moca

Condo near Mass Moca

3 bedrooms·2 baths
North Adams • Massachusetts
4.83(6 reviews)

$940.00 USD total for 3 nights

Oct 20 – 23, 2026

Entrance
Sun Room
Front Entrance Spring 2025
Sunroom entrance
Kitchen

Holly Tree Haven

3 bedrooms·1 bath
Oak Bluffs • Massachusetts

$3,258.45 USD total for 5 nights

Jul 30 – Aug 4, 2027

Little Elm Cottage image 1
Little Elm Cottage image 2
Little Elm Cottage image 3
Little Elm Cottage image 4
Little Elm Cottage image 5

Little Elm Cottage

2 bedrooms·1 bath
Dartmouth • Massachusetts
5(11 reviews)

$985.00 USD total for 3 nights

Oct 25 – 28, 2026

Main Enteance
Enclosed Porch
AT THE CORNER
Deck, Bbq Grill, & Porch
Up Stairs Loft

WALK to WELLFLEET’s INDIAN NECK BEACH

3 bedrooms·2 baths
Wellfleet • Massachusetts
$275/ night(excl. fees & taxes)
Beautiful, inviting, and classic but modern.
Chef's kitchen, fully equipped. Gas stove.
Open plan.
Comfortable communal dining.
Dining outdoors, either on the deck or at the firepit.

The Map House - Modern Wellfleet Vacation

3 bedrooms·2 baths
Wellfleet • Massachusetts
5(3 reviews)

$1,230.34 USD total for 3 nights

Oct 20 – 23, 2026

Charming Family-Friendly, 3+ Bedroom, Farmhouse
Sunny kitchen with water filter on fridge and new stove in 2022. See other photos for close up of the new stove.
Charming Family-Friendly, 3+ Bedroom, Farmhouse
Bertazzoni gas range and electric oven installed in 2022 with superfast boil and pizza setting on the oven.
Sunny bright cook's kitchen is a delight to use. You'll find spices, gadgets, Kitchenaid mixer, blenders etc. New Bertazzoni gas range ‘22

Charming Family-Friendly, 3+ Bedroom, Farmhouse

4 bedrooms·2 baths
Orleans • Massachusetts
4.97(39 reviews)

$3,783.50 USD total for 4 nights

Oct 20 – 24, 2026

Welcome to "Nantucklet," in the heart of Nantucket town!
The living room has a beam in the celiling with writings from the 1800's
Watch TV
Listen to music
Chat with your friends and family

Nantucklet

3 bedrooms·2 baths
Nantucket • Massachusetts
4.96(23 reviews)

$4,033.50 USD total for 3 nights

Oct 20 – 23, 2026

After a day on the slopes, head straight to John Harvard’s. Just upstairs, no driving, no cooking, just comfort, delicious food, and crackling warmth.
Just steps from the slopes, our building sits at the base of Jiminy Peak’s 45 ski trails. Ski-in/ski-out convenience all winter long.
Winter at Jiminy Peak: Slopes, Skiers & Fireside Warmth. Ski-in/ski-out convenience meets cozy aprs-ski vibes.
Spacious bedroom/King Bed with New Mattress & Natural Light
Comfortable Open Floor Plan - Great for Long Stays!

Ski-in/Ski-out 1BR Condo at Jiminy Peak

1 bedroom·1 bath
Hancock • Massachusetts

$3,000.00 USD total for 30 nights

Mar 7 – Apr 6, 2027

our place from the beach
full bath
twin beds, back left
Beach Bridge
House front from yard

Beach Bridge

3 bedrooms·1 bath
Gloucester • Massachusetts

$4,235.00 USD total for 7 nights

Oct 20 – 27, 2026

West Wing of the Captain Morse House
West is on the Left - East is on the right
West Wing and lawn
West and East 8 person patio tables
Patio and Lawn

West Wing of the Captain Morse House

6 bedrooms·4 baths
Edgartown • Massachusetts

$4,849.12 USD total for 3 nights

Oct 31 – Nov 3, 2026

Casa Castor • Private Room 3
Casa Castor • Private Room 3
Casa Castor • Private Room 3
Casa Castor • Private Room 3
Casa Castor • Private Room 3

Casa Castor • Private Room 3

1 bedroom·1 bath
Chelsea • Massachusetts

$370.80 USD total for 3 nights

Oct 20 – 23, 2026

Walk to everything in town - no car needed!
Walk to everything in town - no car needed!
Walk to everything in town - no car needed!
Walk to everything in town - no car needed!
Walk to everything in town - no car needed!

Walk to everything in town - no car needed!

3 bedrooms·1 bath
Nantucket • Massachusetts
4.94(17 reviews)

$4,095.00 USD total for 3 nights

Oct 20 – 23, 2026

East Wing of the Captain Morse House
East Wing of the Captain Morse House
Front Door
Front Porch - 1st floor
View down Morse to the harbor

East Wing of the Captain Morse House

6 bedrooms·3 baths
Edgartown • Massachusetts

$5,332.62 USD total for 3 nights

Oct 21 – 24, 2026

Thompson House Cape Cod
Thompson House Cape Cod
Thompson House Cape Cod
Thompson House Cape Cod
Full kitchen

Thompson House Cape Cod

2 bedrooms·1 bath
Yarmouth • Massachusetts
3(2 reviews)

$3,815.69 USD total for 7 nights

Oct 20 – 27, 2026

Studio in Heart of Beacon Hill (Downtown Boston)
Studio in Heart of Beacon Hill (Downtown Boston)
Studio in Heart of Beacon Hill (Downtown Boston)
Studio in Heart of Beacon Hill (Downtown Boston)
Studio in Heart of Beacon Hill (Downtown Boston)

Studio in Heart of Beacon Hill (Downtown Boston)

1 bedroom·1 bath
Boston • Massachusetts

$1,181.00 USD total for 3 nights

Oct 22 – 25, 2026

Casa Castor • Private Room 1
Casa Castor • Private Room 1
Casa Castor • Private Room 1
Casa Castor • Private Room 1
Casa Castor • Private Room 1

Casa Castor • Private Room 1

1 bedroom·1 bath
Chelsea • Massachusetts

$370.80 USD total for 3 nights

Oct 20 – 23, 2026

Sea Glenn Flowers
Full Kitchen
Primary Bedroom Suite 2nd Floor
Sea Glenn Flowers
Sea Glenn Flowers Vacation Home

Sea Glenn Flowers Vacation Home

4 bedrooms·3 baths
Oak Bluffs • Massachusetts

$2,132.23 USD total for 3 nights

Oct 20 – 23, 2026

Berkshires Cottage | Trails & Water Nearby
Berkshires Cottage | Trails & Water Nearby
Berkshires Cottage | Trails & Water Nearby
Berkshires Cottage | Trails & Water Nearby
Fully stocked eat-in kitchen

Berkshires Cottage | Trails & Water Nearby

2 bedrooms·1 bath
Monterey • Massachusetts

$632.79 USD total for 3 nights

Oct 20 – 23, 2026

Casa Castor • Private Room 2
Casa Castor • Private Room 2
Casa Castor • Private Room 2
Casa Castor • Private Room 2
Casa Castor • Private Room 2

Casa Castor • Private Room 2

1 bedroom·1 bath
Chelsea • Massachusetts

$370.80 USD total for 3 nights

Oct 20 – 23, 2026

Jiminy Peak Slopeside Getaway • Ski & Adventure
Jiminy Peak Slopeside Getaway • Ski & Adventure
Jiminy Peak Slopeside Getaway • Ski & Adventure
Jiminy Peak Slopeside Getaway • Ski & Adventure
Jiminy Peak Slopeside Getaway • Ski & Adventure

Jiminy Peak Slopeside Getaway • Ski & Adventure

2 bedrooms·2 baths
Hancock • Massachusetts

$820.88 USD total for 3 nights

Oct 22 – 25, 2026

Entrance on North Water St
Main House from Pool House
Back Entrance to Main House
Back Patio
Kitchen

Connaught House Luxury North Water Street enclave with pool

6 bedrooms·5½ baths
Edgartown • Massachusetts

$31,754.08 USD total for 7 nights

Oct 24 – 31, 2026

Outermost Penninsula w cottage to left
Main House
Outermost Penninsula view to Edgartown
Living Room fireplace
Super Moon Rising over Main House

Outermost House

6 bedrooms·5½ baths
Edgartown • Massachusetts

$15,185.00 USD $14,066.85 USD total for 7 nights

Oct 20 – 27, 2026