2BR Cottage Vacation Rental in Chatham, Massachusetts

Vacation Rentals

Updated on May 23, 2020

NEW! Mill Pond Artist Cottage Walk to Town & Beach!

Located in: Chatham
Incredibly charming historic property in Chatham's Old Village neighborhood. Short walk to town and beach as well as the Chatham Lighthouse from this property. This classic property was once a Cobbler's Shop on Main St. Relocated to this site in the 1940's, the famous Artist Cottage is steeped in history and has been fully renovated and updated with a new bathroom and kitchenette while painstakingly retaining the unique character of this charming cottage, particularly it's historic murals .
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"Cape Escape" Sunny Renovated House - Walk To Beach & Tennis, Central AC/WiFi

3 bedroom house in Chatham, MA

Walking Distance to beach with peek-a-boo views of water and Nantucket Sound. Everything's new in this home with separate living room and family room both with HD TV and Wifi. After a day of sun and...

Lovely Home-Downtown Chatham-Walk to everything! 48 Seaview Street Chatham

3 bedroom house in Chatham, MA

Enjoy the downtown location of this Cape Cod Vacation Rental Home in the village of Chatham. Convenient to Chatham shops, restaurants, new Orpheum movie theatre and Oyster Pond. Families love the...

Beautiful Spacious Centrally Located Condo *Available Independence Day Week!*

2 bedroom condo in Chatham, MA

This spacious 1200 s.f. condominium is just one block from Commercial street located above Far Land General Store. This unit is filled with loads of natural light and has two bedrooms and two full...

Attractive Cape close to bike path, beaches, tennis courts

4 bedroom house in Chatham, MA

You will not find a better vacation home at this price! Great house for families. Well appointed home located in a lovely bayside neighborhood with access to Association tennis courts and The Cape Cod...

2016 Renovation - Charming & Quaint Cottage, Steps to Beach, Shops, & Nightlife

1 bedroom cottage in Chatham, MA

166 Bradford Street, #3 RENOVATED SPRING 2016 This historic cottage is perfect for your relaxing vacation or visit to Provincetown. Our cottage is located near the center of town on Bradford Street...

Near Orleans Center with water views and a heated Pool! 039-O; sleeps 24

10 bedroom house in Chatham, MA

This property is professionally managed by Pretty Picky Properties. "Second Wind" -- An Orleans estate with large heated pool, on Town Cove Week of 4th of July Special -- rate reduced $4,000 for...

Book it now! Clean cute family-friendly Ocean Edge cond

2 bedroom condo in Chatham, MA

We are inviting you and your family to spend a great time in this cute Ocean Edge condo. It is clean, comfortable and very well maintained. This garden end unit features 2 bedrooms, 2 updated full...

Classic Cape Cod Beach Cottage With Waterviews,steps To Beach

3 bedroom cottage in Chatham, MA

Welcome to 'THE SAND DUNE' BEACH COTTAGE ,our bright and airy year round 2 story cottage offers 3 BR , 2 Baths ,sleeps five comfortably. There are two parking spaces off street next to house. It has...


3 bedroom house in Chatham, MA

***Due to the coronavirus, we’re taking extra care to disinfect frequently touched surfaces between reservations.*** WHOLE HOUSE A/C EACH BEDROOM HAS ITS OWN TEMPERATURE CONTROL MASTER...

#506: Steps to Private Neighborhood Beach! Roof Deck w/ Views, Large Yard!

3 bedroom house in Chatham, MA

SAVINGS: ANY stay of 32+ nights For All Dates will be prioritized over the current availability shown on the calendar, and, receive a discount of AT LEAST 35% OFF - If you intend to stay for this...

Amazing Location For 3 Bed 2 Bath Town Home On 5 Levels (2 1/2 Stories Tall) #B

3 bedroom townhome in Chatham, MA

The town house features sunny exposures with wonderful water views, newer oak floors throughout,fully air conditioned (split a/c where every room can be controlled) , wireless internet, parking for...

#105: Beachfront on Commercial St w/ Sweeping Views of the Harbor! Dog Friendly!

4 bedroom house in Chatham, MA

SAVINGS: for any stay of 32+ nights (these inquiries will be prioritized over the current availability shown on the calendar). Call or message us to learn how you can save up to 35%+ OFF standard...

Attractive Contemporary 3BR Wellfleet Home with AC

3 bedroom house in Chatham, MA

Spacious Contemporary Wellfleet home located in a quiet area near Lt. Island. This home is unique with its use of a new multi-level deck. Enjoy the screened porch and places for privacy and lots of...

Large home w/ central air, breathtaking water views and spectacular sunsets

6 bedroom house in Chatham, MA

Large, newly renovated home on a large private lot in a family friendly neighborhood. The home sits atop the highest point in North Chatham with views of Crows Pond (salt water inlet), Pleasant Bay,...

New construction home on quiet, private waterview lot near Pleasant Bay

2 bedroom house in Chatham, MA

This cozy, immaculate, recently-constructed home sits on an very private half-acre lot in a quiet, upscale neighborhood in South Orleans. A regular summer-long renter had to cancel. We welcome...

2C Dean- Central AC added for 2020! .3 mile walk to sandy beach!

2 bedroom house in Chatham, MA

THIS PROPERTY RENTS SATURDAY THROUGH SATURDAY. YOU MUST BOOK IN 7 NIGHT INCREMENTS. Inviting ocean breezes and Nantucket Sound views from the upper level of this home. Located at the end of a dead...

31 Cornell- Window ac in each bedroom, updated bathroom, 12x24 deck with grill

3 bedroom house in Chatham, MA

THIS PROPERTY RENTS SATURDAY THROUGH SATURDAY. YOU MUST BOOK IN 7 NIGHT INCREMENTS. Pleasant three bedroom home near Haigis Beach. Nice sun porch and a 14’x24’ rear deck with gas grill. Window...

By The Bay-Memories Made Here!

4 bedroom house in Chatham, MA

Welcome to Laddy’s Retreat! This home is freshly decorated and lovingly maintained year round and offers every amenity needed for that memorable family vacation! It is located just less than 1.1...

Nice South Eastham with Central Air Near Bike Trail

3 bedroom house in Chatham, MA

New Listing 2019 Comfortable and spacious home with quaint farmer's porch nestled on a nicely wooded lot just 3/10ths of a mile to the Cape Cod Rail Bike Trail. Enter the first floor to find a...

Pool, Beach Pass, Walk to Osterville Village, Steps to Joshuas Pond

3 bedroom house in Chatham, MA

Location, location, location! Beautiful, spacious quintessential Cape Cod home perfect for multigenerational families. You can lounge by the salt water pool while the kids bike ride or walk to...
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