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Budget to luxury Chatham, Massachusetts travel and vacations. Search all the best vacation options in Chatham including accommodations, adventure travel, unique tours and much more.


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Featured Listings

1 - 20 of 32 within 100 miles of Chatham, Massachusetts
Captain's House Inn Chatham, Massachusetts Bed & Breakfasts

Captain's House Inn

Chatham, Massachusetts Bed & Breakfasts
This elegant AAA Four Diamond sea captain's estate is the perfect choice for a romantic getaway. Featuring 16 luxurious rooms with 4 poster beds, fireplaces, whirlpools, TV/DVDs full breakfast and 2 a...
From USD $185 per night
Holiday Inn Select Boston - Government Center Boston, Massachusetts Hotels & Resorts

Holiday Inn Select Boston - Government Center

Boston, Massachusetts Hotels & Resorts - 87.5 miles away
Boston travel has a rich and colorful history. Also, an unparalleled array of thrilling attractions. One of America's most engaging cities, Boston is truly a town of superlatives. ...
From USD $269 per night

Hyannis House Hyannis , Massachusetts Vacation Rentals

Hyannis House

Hyannis , Massachusetts Vacation Rentals - 15.8 miles away
Bedrooms: 3  Sleeps: 6  Bathrooms: 2  
Cape Cod - Hyannis. 3 bdr 2 bth house. Walk to 3 beaches, center, Kennedy Mem.& harbor. Drive to movies,golf, malls. w/d;d/w, cable & VCR, patio yrd with grill, beach chairs and linens. /no pets/no s...
From USD $2,500 per week
Inn at Cape Cod Yarmouth Port, Massachusetts Bed & Breakfasts

Inn at Cape Cod

Yarmouth Port, Massachusetts Bed & Breakfasts - 13.8 miles away
This exquisite 9 roomed bed and breakfast inn is located in mid Cape Cod. All rooms and suites have private bath, some have fireplace/massage tub/private balcony. Walk to restaurants, beach, shops and...
From USD $205 per night
A Bunker Hill Bed and Breakfast Boston, Massachusetts Bed & Breakfasts

A Bunker Hill Bed and Breakfast

Boston, Massachusetts Bed & Breakfasts - 72.3 miles away
A truly victorian B & B with all amenities-just bring yourself - YOUR HOME AWAY FROM HOME- in the heart of Boston near the historical waterfront district just off the Freedom Trail....
From USD $135 per night
Sylvan Rentals Chatham, Cape Cod, Massachusetts Vacation Rentals

Sylvan Rentals

Chatham, Cape Cod, Massachusetts Vacation Rentals - 87.5 miles away
Bedrooms: 3  Sleeps: 8  Bathrooms: 2  
Sylvan Rentals is the exclusive agent for some 200 vacation rental homes in the towns of Chatham and Harwich. Waterfront, waterview, walk to beach and town. These are fully-furnished privately owned p...
Contact For Rates & Specials!
Celeb Owned Hilltop Waterview Retreat Chilmark, Massachusetts Vacation Rentals

Celeb Owned Hilltop Waterview Retreat

Chilmark, Massachusetts Vacation Rentals - 46.4 miles away
Bedrooms: 4  
This unique, celeb owned, hilltop waterview, lofty retreat offers privacy, and hot tub. For a full listiing go to Home away dot com....
Contact For Rates & Specials!
Deer Run French Country Style Farmhouse / Hot Tub Chilmark, Massachusetts Vacation Rentals

Deer Run French Country Style Farmhouse / Hot Tub

Chilmark, Massachusetts Vacation Rentals - 46.9 miles away
Bedrooms: 3  Sleeps: 7  Bathrooms: 2  
Post and Beam Farmhouse with Hot Tub on edge of Woodland close to some of MARTHA'S VINEYARD ISLANDS most coveted - Lucy Vincent Beach and Squibnocket, close to Aquinnah Beaches and Gay head Light....
From USD $500 per night
Hawthorne Inn- Relaxed elegance Concord, Massachusetts Bed & Breakfasts

Hawthorne Inn- Relaxed elegance

Concord, Massachusetts Bed & Breakfasts - 87.5 miles away
Recognized by Forbes: “10 Best Inns of New England.” and "Top 14" by Frommers. Artwork filled B&B where Nature, Literature and History entwine. Seven vibrant Guestrooms & Multi-course Breakfast. ...
From USD $199 per night
'By the Sea' Guests Bed & Breakfast & Suites Dennis Port, Massachusetts Bed & Breakfasts

'By the Sea' Guests Bed & Breakfast & Suites

Dennis Port, Massachusetts Bed & Breakfasts - 11.5 miles away
Oceanfront B&B with private beach an Breakfast served overlooking Nantucket Sound on 100' wraparound glass-screened porch. 12 comfortable, non-smoking, rooms with private baths. We offer you Sea, San...
From USD $175 per night
Catch Giant Bluefin Tuna, Sweet Dream Sportfishing Gloucester, Massachusetts Fishing Trips

Catch Giant Bluefin Tuna, Sweet Dream Sportfishing

Gloucester, Massachusetts Fishing Trips - 73.4 miles away
Catch School Tuna, Giant Bluefin Tuna, Cod and Haddock, Halibut, Striped Bass, Bluefish and Sharks on the fast and comfortable 38' F/V SWEET DREAM. Fishing from historic Gloucester Massachusetts....
From USD $650 per trip

Birchwood Inn- Best Breakfast in New England Lenox, Massachusetts Bed & Breakfasts

Birchwood Inn- Best Breakfast in New England

Lenox, Massachusetts Bed & Breakfasts - 87.5 miles away
Comfortable and timeless elegance in a romantic 1767 bed and breakfast inn. 11 warm and welcoming guestrooms, 9 fireplaces, fireside library, shady porch, stone-fenced gardens, and "best breakfast in ...
From USD $180 per night
The Laurel, a 2BR and or 1BR Guest House Truro, Massachusetts Vacation Rentals

The Laurel, a 2BR and or 1BR Guest House

Truro, Massachusetts Vacation Rentals - 21.1 miles away
Bedrooms: 2  Sleeps: 5  Bathrooms: 2  
Our homes are on a secluded, two-acre lot overlooking Cape Cod National Seashore. The 2BR main house is described here The beautiful handcrafted 1 BR guest house is available separately....
From USD $975 per week
Northern Exposure Nantucket Nantucket, Massachusetts Vacation Rentals

Northern Exposure Nantucket

Nantucket, Massachusetts Vacation Rentals - 29.2 miles away
Bedrooms: 4  Sleeps: 8  Bathrooms: 2  
Northern Exposure was built in 1994 and is a very bright and well furnished "New England Upside-Down House" (with living areas upstairs, and bedrooms downstairs) just 0.9 mile from the Main Street. Na...
From USD $2,500 per week
hot travel deals
A Beach House Oceanfront Bed & Breakfast Plymouth, Massachusetts Bed & Breakfasts

A Beach House Oceanfront Bed & Breakfast

Plymouth, Massachusetts Bed & Breakfasts - 30.5 miles away
Guests call The Beach House "A dream of a place... a little bit of paradise." Others claim it, we're Plymouth's only B&B at the ocean's edge. Casual elegance, an unforgettable view...sunrises, sailboa...
From USD $195 per night
Fuller Craft Museum Brockton, Massachusetts Artisan & Trade Workshops

Fuller Craft Museum

Brockton, Massachusetts Artisan & Trade Workshops - 61.9 miles away
Fuller Craft is a dynamic environment where craft is experienced through exhibitions, education, outreach and collaboration. We explore the materials, techniques and artistic expression that challenge...
From USD $8 per trip
Relaxing Weekend Getaways Plymouth, Massachusetts Hotels & Resorts

Relaxing Weekend Getaways

Plymouth, Massachusetts Hotels & Resorts - 42.0 miles away
The Hampton Inn & Suites Plymouth MA will provide an oasis from the hustle & bustle of city life. Just a short drive South of Boston,relax in our mini-suites , enjoy our glass enclosed heated pool & w...
From USD $99 per night


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