PRIVATE BEACH Bay views image 1
Comfortable cottage with bay views on a private beach.
PRIVATE BEACH Bay views image 3
The view from your cottage. Bay views and Sunsets over the water.
Your private beach looking west

PRIVATE BEACH Bay views

2 bedrooms·1 bath
Brewster • Massachusetts
4.98(87 reviews)
$550 – $650/ nacht(excl. kosten & belastingen)
Entrance
Sun Room
Front Entrance Spring 2025
Sunroom entrance
Kitchen

Holly Tree Haven

3 bedrooms·1 bath
Oak Bluffs • Massachusetts

$ 3.258,45 USD totaal voor 5 nachten

30 jul – 4 aug 2027

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/ nacht(excl. kosten & belastingen)
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)

$ 1.320,00 USD totaal voor 3 nachten

25–28 sep 2026

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)
$200 – $425/ nacht(excl. kosten & belastingen)
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 totaal voor 4 nachten

25–29 sep 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)

$ 4.237,00 USD totaal voor 3 nachten

25–28 sep 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 totaal voor 30 nachten

7 mrt – 6 apr 2027

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)

$ 4.495,00 USD totaal voor 3 nachten

25–28 sep 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

$ 4.577,30 USD totaal voor 3 nachten

28 sep – 1 okt 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

$ 6.480,25 USD totaal voor 3 nachten

28 sep – 1 okt 2026

Vienna House
Front Porch
Side Porch and Parking
Kitchen
Kitchen & island

Vienna Ave House

3 bedrooms·2 baths
Oak Bluffs • Massachusetts

$ 3.096,37 USD totaal voor 3 nachten

25–28 sep 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 totaal voor 7 nachten

25 sep – 2 okt 2026

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 totaal voor 7 nachten

25 sep – 2 okt 2026

Cozy Queen Room w/ Partial Ocean View (202)
Cozy Queen Room w/ Partial Ocean View (202)
Cozy Queen Room w/ Partial Ocean View (202)
Cozy Queen Room w/ Partial Ocean View (202)
Cozy Queen Room w/ Partial Ocean View (202)

Cozy Queen Room w/ Partial Ocean View (202)

0 bedrooms·1 bath
Falmouth • Massachusetts

$ 1.391,93 USD totaal voor 3 nachten

25–28 sep 2026

Partial Ocean View Studio with Large Private Deck (307)
Partial Ocean View Studio with Large Private Deck (307)
Partial Ocean View Studio with Large Private Deck (307)
Partial Ocean View Studio with Large Private Deck (307)
Partial Ocean View Studio with Large Private Deck (307)

Partial Ocean View Studio with Large Private Deck (307)

0 bedrooms·1 bath
Falmouth • Massachusetts

$ 1.601,21 USD totaal voor 3 nachten

25–28 sep 2026

Renovated Queen Room Near the Beach (310)
Renovated Queen Room Near the Beach (310)
Renovated Queen Room Near the Beach (310)
Renovated Queen Room Near the Beach (310)
Renovated Queen Room Near the Beach (310)

Renovated Queen Room Near the Beach (310)

0 bedrooms·1 bath
Falmouth • Massachusetts

$ 1.348,33 USD totaal voor 3 nachten

25–28 sep 2026

Spacious 1-Bedroom with King & Double Beds (301)
Spacious 1-Bedroom with King & Double Beds (301)
Spacious 1-Bedroom with King & Double Beds (301)
Spacious 1-Bedroom with King & Double Beds (301)
Spacious 1-Bedroom with King & Double Beds (301)

Spacious 1-Bedroom with King & Double Beds (301)

1 bedroom·1 bath
Falmouth • Massachusetts

$ 2.048,11 USD totaal voor 3 nachten

25–28 sep 2026

Cozy Queen Studio – Walk to the Beach (303)
Cozy Queen Studio – Walk to the Beach (303)
Cozy Queen Studio – Walk to the Beach (303)
Cozy Queen Studio – Walk to the Beach (303)
Cozy Queen Studio – Walk to the Beach (303)

Cozy Queen Studio – Walk to the Beach (303)

0 bedrooms·1 bath
Falmouth • Massachusetts

$ 1.250,23 USD totaal voor 3 nachten

25–28 sep 2026

Partial Ocean View Studio | 2 Doubles + Kitchenette (107)
Partial Ocean View Studio | 2 Doubles + Kitchenette (107)
Partial Ocean View Studio | 2 Doubles + Kitchenette (107)
Partial Ocean View Studio | 2 Doubles + Kitchenette (107)
Partial Ocean View Studio | 2 Doubles + Kitchenette (107)

Partial Ocean View Studio | 2 Doubles + Kitchenette (107)

0 bedrooms·1 bath
Falmouth • Massachusetts

$ 1.119,43 USD totaal voor 3 nachten

25–28 sep 2026

Beachfront Studio | Kitchenette & 2 Double Beds (104)
Beachfront Studio | Kitchenette & 2 Double Beds (104)
Beachfront Studio | Kitchenette & 2 Double Beds (104)
Beachfront Studio | Kitchenette & 2 Double Beds (104)
Beachfront Studio | Kitchenette & 2 Double Beds (104)

Beachfront Studio | Kitchenette & 2 Double Beds (104)

0 bedrooms·1 bath
Falmouth • Massachusetts

$ 1.282,93 USD totaal voor 3 nachten

25–28 sep 2026

Direct Ocean Views! Studio with Kitchenette & Shared Deck (106)
Direct Ocean Views! Studio with Kitchenette & Shared Deck (106)
Direct Ocean Views! Studio with Kitchenette & Shared Deck (106)
Direct Ocean Views! Studio with Kitchenette & Shared Deck (106)
Direct Ocean Views! Studio with Kitchenette & Shared Deck (106)

Direct Ocean Views! Studio with Kitchenette & Shared Deck (106)

0 bedrooms·1 bath
Falmouth • Massachusetts

$ 1.797,41 USD totaal voor 3 nachten

25–28 sep 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 totaal voor 3 nachten

22–25 okt 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

$ 17.842,68 USD $ 16.511,91 USD totaal voor 7 nachten

25 sep – 2 okt 2026