Vacation rentals in Dukes County, MA

89 available vacation rental offers

airbnbBooking.comVrboExpediaSonderpricelineTripadvisorTrip.comHomestayHotels.comOrbitz

Choose the perfect vacation accommodation

Price per night

Up to $100$100 - 200From $200

Accommodation type

Vacation rentals and Airbnb

Rating

Excellent 9+Very good 8+Good 7+All ratings

Best vacation rentals and Airbnb offers in Dukes County, MA

Island Getaway - Dukes County, MA

Island Getaway

Holiday Home, Dukes County

Island Getaway is a holiday home in Dukes County. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Read more

About Island Getaway

Island Getaway is a holiday home in Dukes County. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: ac, air conditioning, heating, and garden.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,079.

From$362/night
Show
Private cottage nestled in center of the Vineyard - Dukes County, MA

Private cottage nestled in center of the Vineyard

Holiday Home, Dukes County

Private cottage nestled in center of the Vineyard is a holiday home in Dukes County, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

Read more

About Private cottage nestled in center of the Vineyard

Private cottage nestled in center of the Vineyard is a holiday home in Dukes County, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,788.

From$398/night
Show
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs - Dukes County, MA

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Holiday Home, Dukes County

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs is a holiday home in Dukes County, with easy beach access, outdoor space, and kitchen access. This stay gives…

Read more

About Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs is a holiday home in Dukes County, with easy beach access, outdoor space, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,259.

From$466/night
Show
Quiet 2-bedroom cottage in Chilmark, MA Martha's Vineyard - Dukes County, MA

Quiet 2-bedroom cottage in Chilmark, MA Martha's Vineyard

Cottage, Dukes County

Quiet 2-bedroom cottage in Chilmark, MA Martha's Vineyard is a cottage in Dukes County, with room for a group and a quieter setting. This stay gives travelers a comfortable base for…

Read more

About Quiet 2-bedroom cottage in Chilmark, MA Martha's Vineyard

Quiet 2-bedroom cottage in Chilmark, MA Martha's Vineyard is a cottage in Dukes County, with room for a group and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: laundry service, non smoking, and shower.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,508.

From$501/night
Show

Vacation rentals with a pool in Dukes County, MA

Add a pool to the search when you want an easy place to cool off between outings.

Great two house compound, inground pool, great privacy - Dukes County, MA

Great two house compound, inground pool, great privacy

Holiday Home, Dukes County

Great two house compound, inground pool, great privacy is a holiday home in Dukes County, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the…

Read more

About Great two house compound, inground pool, great privacy

Great two house compound, inground pool, great privacy is a holiday home in Dukes County, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $8,063.

From$1,152/night
Show
4 BDR house with CUSTOM POOL, SPA and FIRE PIT in Edgartown. - Dukes County, MA

4 BDR house with CUSTOM POOL, SPA and FIRE PIT in Edgartown.

Holiday Home, Dukes County

4 BDR house with CUSTOM POOL, SPA and FIRE PIT in Edgartown. is a holiday home in Dukes County, with pool access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About 4 BDR house with CUSTOM POOL, SPA and FIRE PIT in Edgartown.

4 BDR house with CUSTOM POOL, SPA and FIRE PIT in Edgartown. is a holiday home in Dukes County, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, washer, dryer, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $12,225.

From$1,746/night
Show
Beautiful 4 Bedroom House with Private Pool and Private Beach Access - Dukes County, MA

Beautiful 4 Bedroom House with Private Pool and Private Beach Access

Holiday Home, Dukes County

Beautiful 4 Bedroom House with Private Pool and Private Beach Access is a holiday home in Dukes County, with pool access, easy beach access, and kitchen access. This stay gives travelers a…

Read more

About Beautiful 4 Bedroom House with Private Pool and Private Beach Access

Beautiful 4 Bedroom House with Private Pool and Private Beach Access is a holiday home in Dukes County, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $12,754.

From$1,822/night
Show
Cool, Mid-Century House -- Lucy Vincent Beach and Pool!!! - Dukes County, MA

Cool, Mid-Century House -- Lucy Vincent Beach and Pool!!!

Holiday Home, Dukes County

Cool, Mid-Century House -- Lucy Vincent Beach and Pool!!! is a holiday home in Dukes County, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base…

Read more

About Cool, Mid-Century House -- Lucy Vincent Beach and Pool!!!

Cool, Mid-Century House -- Lucy Vincent Beach and Pool!!! is a holiday home in Dukes County, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $16,658.

From$2,380/night
Show

Vacation rentals with parking in Dukes County, MA

Find vacation rentals that make arriving by car easier.

Vineyard Haven Oasis! - Dukes County, MA

Vineyard Haven Oasis!

Holiday Home, Dukes County

Vineyard Haven Oasis! is a holiday home in Dukes County, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

Read more

About Vineyard Haven Oasis!

Vineyard Haven Oasis! is a holiday home in Dukes County, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,334.

From$762/night
Show
Sunny Vineyard Getaway Close to Everything steps from sound clean and comfy - Dukes County, MA

Sunny Vineyard Getaway Close to Everything steps from sound clean and comfy

Holiday Home, Dukes County

Sunny Vineyard Getaway Close to Everything steps from sound clean and comfy is a holiday home in Dukes County, with parking and kitchen access. This stay gives travelers a comfortable base…

Read more

About Sunny Vineyard Getaway Close to Everything steps from sound clean and comfy

Sunny Vineyard Getaway Close to Everything steps from sound clean and comfy is a holiday home in Dukes County, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,359.

From$766/night
Show
Spacious family house, short walk to the Lagoon & close to Oak Bluffs center - Dukes County, MA

Spacious family house, short walk to the Lagoon & close to Oak Bluffs center

Holiday Home, Dukes County

Spacious family house, short walk to the Lagoon & close to Oak Bluffs center is a holiday home in Dukes County, with parking, kitchen access, and room for a group. This stay gives travelers…

Read more

About Spacious family house, short walk to the Lagoon & close to Oak Bluffs center

Spacious family house, short walk to the Lagoon & close to Oak Bluffs center is a holiday home in Dukes County, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,533.

From$790/night
Show
Secluded retreat in Seven Gates Farm on 7 Acres, Private Beach, Tennis, Pond - Dukes County, MA

Secluded retreat in Seven Gates Farm on 7 Acres, Private Beach, Tennis, Pond

Holiday Home, Dukes County

Secluded retreat in Seven Gates Farm on 7 Acres, Private Beach, Tennis, Pond is a holiday home in Dukes County, with pet-friendly space, easy beach access, and parking. This stay gives…

Read more

About Secluded retreat in Seven Gates Farm on 7 Acres, Private Beach, Tennis, Pond

Secluded retreat in Seven Gates Farm on 7 Acres, Private Beach, Tennis, Pond is a holiday home in Dukes County, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $8,408.

From$1,201/night
Show

Pet-friendly vacation rentals in Dukes County, MA

Bring your pet along with stays that welcome four-legged travelers.

Private setting nestled in the heart of East Chop. - Dukes County, MA

Private setting nestled in the heart of East Chop.

Holiday Home, Dukes County

Private setting nestled in the heart of East Chop. is a holiday home in Dukes County, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring…

Read more

About Private setting nestled in the heart of East Chop.

Private setting nestled in the heart of East Chop. is a holiday home in Dukes County, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,160.

From$737/night
Show
Edgartown - Vacation Home In A Great Location!!!! - Dukes County, MA

Edgartown - Vacation Home In A Great Location!!!!

Holiday Home, Dukes County

Edgartown - Vacation Home In A Great Location!!!! is a holiday home in Dukes County, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

Read more

About Edgartown - Vacation Home In A Great Location!!!!

Edgartown - Vacation Home In A Great Location!!!! is a holiday home in Dukes County, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,503.

From$786/night
Show
West Tisbury Gem with Association Pool + Hiking Trails, Close to All - Dukes County, MA

West Tisbury Gem with Association Pool + Hiking Trails, Close to All

Holiday Home, Dukes County

West Tisbury Gem with Association Pool + Hiking Trails, Close to All is a holiday home in Dukes County, with pet-friendly space and pool access. This stay gives travelers a comfortable base…

Read more

About West Tisbury Gem with Association Pool + Hiking Trails, Close to All

West Tisbury Gem with Association Pool + Hiking Trails, Close to All is a holiday home in Dukes County, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $6,167.

From$881/night
Show
5-bedroom, 3-bath house on 5 Acres in Chilmark - Dukes County, MA

5-bedroom, 3-bath house on 5 Acres in Chilmark

Holiday Home, Dukes County

5-bedroom, 3-bath house on 5 Acres in Chilmark is a holiday home in Dukes County, with pet-friendly space and room for a group. This stay gives travelers a comfortable base for exploring…

Read more

About 5-bedroom, 3-bath house on 5 Acres in Chilmark

5-bedroom, 3-bath house on 5 Acres in Chilmark is a holiday home in Dukes County, with pet-friendly space and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $7,351.

From$1,050/night
Show

Vacation rentals with a kitchen in Dukes County, MA

Compare stays with kitchen access for longer trips and easier meals.

Quaint, ranch style home in Oak Bluffs with central air - Dukes County, MA

Quaint, ranch style home in Oak Bluffs with central air

Holiday Home, Dukes County

Quaint, ranch style home in Oak Bluffs with central air is a holiday home in Dukes County, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Quaint, ranch style home in Oak Bluffs with central air

Quaint, ranch style home in Oak Bluffs with central air is a holiday home in Dukes County, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,803.

From$543/night
Show
Gorgeous home near the ocean w/ a full kitchen, deck, & large, fenced back yard - Dukes County, MA

Gorgeous home near the ocean w/ a full kitchen, deck, & large, fenced back yard

Holiday Home, Dukes County

Gorgeous home near the ocean w/ a full kitchen, deck, & large, fenced back yard is a holiday home in Dukes County, with easy beach access, outdoor space, and kitchen access. This stay gives…

Read more

About Gorgeous home near the ocean w/ a full kitchen, deck, & large, fenced back yard

Gorgeous home near the ocean w/ a full kitchen, deck, & large, fenced back yard is a holiday home in Dukes County, with easy beach access, outdoor space, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, fireplace, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,873.

From$553/night
Show
Oak Bluffs Home with Renovated Screened-in Porch - Short Drive to Beach - Dukes County, MA

Oak Bluffs Home with Renovated Screened-in Porch - Short Drive to Beach

Holiday Home, Dukes County

Oak Bluffs Home with Renovated Screened-in Porch - Short Drive to Beach is a holiday home in Dukes County, with easy beach access and kitchen access. This stay gives travelers a comfortable…

Read more

About Oak Bluffs Home with Renovated Screened-in Porch - Short Drive to Beach

Oak Bluffs Home with Renovated Screened-in Porch - Short Drive to Beach is a holiday home in Dukes County, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,042.

From$720/night
Show
3BR House Close to Beach: Large Yard & Deck! - Dukes County, MA

3BR House Close to Beach: Large Yard & Deck!

Cottage, Dukes County

3BR House Close to Beach: Large Yard & Deck! is a cottage in Dukes County, with easy beach access, outdoor space, and kitchen access. This stay gives travelers a comfortable base for…

Read more

About 3BR House Close to Beach: Large Yard & Deck!

3BR House Close to Beach: Large Yard & Deck! is a cottage in Dukes County, with easy beach access, outdoor space, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $6,683.

From$789/night
Show

Family-friendly vacation rentals in Dukes County, MA

Plan a trip with stays that give families more room to spread out.

A Vineyard Home Perfect For Family Gatherings - Dukes County, MA

A Vineyard Home Perfect For Family Gatherings

Holiday Home, Dukes County

A Vineyard Home Perfect For Family Gatherings is a holiday home in Dukes County, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

Read more

About A Vineyard Home Perfect For Family Gatherings

A Vineyard Home Perfect For Family Gatherings is a holiday home in Dukes County, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,592.

From$656/night
Show
Charming Cottage Near West Chop- Vineyard Haven - Dukes County, MA

Charming Cottage Near West Chop- Vineyard Haven

Holiday Home, Dukes County

Charming Cottage Near West Chop- Vineyard Haven is a holiday home in Dukes County, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

Read more

About Charming Cottage Near West Chop- Vineyard Haven

Charming Cottage Near West Chop- Vineyard Haven is a holiday home in Dukes County, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,061.

From$723/night
Show
Cottage w/ water views from front yard, central ac & fireplace - Dukes County, MA

Cottage w/ water views from front yard, central ac & fireplace

Holiday Home, Dukes County

Cottage w/ water views from front yard, central ac & fireplace is a holiday home in Dukes County, with kitchen access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Cottage w/ water views from front yard, central ac & fireplace

Cottage w/ water views from front yard, central ac & fireplace is a holiday home in Dukes County, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, fireplace, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,156.

From$737/night
Show
Stylish In-Town Cottage- Walk to everything! - Dukes County, MA

Stylish In-Town Cottage- Walk to everything!

Holiday Home, Dukes County

Stylish In-Town Cottage- Walk to everything! is a holiday home in Dukes County, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Stylish In-Town Cottage- Walk to everything!

Stylish In-Town Cottage- Walk to everything! is a holiday home in Dukes County, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,350.

From$764/night
Show