Vacation rentals in Pleasant Pond, ME

Best vacation rentals and Airbnb offers in Pleasant Pond, ME

Streamside Campsite plus tiny cabin combines classic camping with rustic charm!!

Cabin, Pleasant Pond

Streamside Campsite plus tiny cabin combines classic camping with rustic charm!! is a cabin in Pleasant Pond, with pet-friendly space, parking, and kitchen access. This stay gives travelers…

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About Streamside Campsite plus tiny cabin combines classic camping with rustic charm!!

Streamside Campsite plus tiny cabin combines classic camping with rustic charm!! is a cabin in Pleasant Pond, 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 $787.

From$112/night

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Quiet rural Maine cabin near Bigelow Preserve, Flagstaff Lake and Sugarloaf

Cabin, Pleasant Pond

Quiet rural Maine cabin near Bigelow Preserve, Flagstaff Lake and Sugarloaf is a cabin in Pleasant Pond, with parking, kitchen access, and a quieter setting. This stay gives travelers a…

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About Quiet rural Maine cabin near Bigelow Preserve, Flagstaff Lake and Sugarloaf

Quiet rural Maine cabin near Bigelow Preserve, Flagstaff Lake and Sugarloaf is a cabin in Pleasant Pond, with parking, kitchen access, 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: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $909.

From$130/night

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Welcome Outdoor Enthusiasts! Direct ATV access.

Holiday Home, Pleasant Pond

Welcome Outdoor Enthusiasts! Direct ATV access. is a holiday home in Pleasant Pond, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Welcome Outdoor Enthusiasts! Direct ATV access.

Welcome Outdoor Enthusiasts! Direct ATV access. is a holiday home in Pleasant Pond, 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 $1,017.

From$145/night

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Post and beam cabin with king and bunk

Cabin, Pleasant Pond

Post and beam cabin with king and bunk is a cabin in Pleasant Pond, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Post and beam cabin with king and bunk

Post and beam cabin with king and bunk is a cabin in Pleasant Pond, 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 cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,077.

From$154/night

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Vacation rentals with a pool in Pleasant Pond, ME

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

Ski In Ski Out Family Friendly Sugarloaf Condo @ Snubber Trail Mid Station on Mt

Condo, Pleasant Pond

Ski In Ski Out Family Friendly Sugarloaf Condo @ Snubber Trail Mid Station on Mt is a condo in Pleasant Pond, with pool access, kitchen access, and room for a group. This stay gives…

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About Ski In Ski Out Family Friendly Sugarloaf Condo @ Snubber Trail Mid Station on Mt

Ski In Ski Out Family Friendly Sugarloaf Condo @ Snubber Trail Mid Station on Mt is a condo in Pleasant Pond, with pool access, 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, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,559.

From$223/night

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Cozy~ON LIFT~Studio~Sugarloaf Views~Walk to it All!

Apartment, Pleasant Pond

Cozy~ON LIFT~Studio~Sugarloaf Views~Walk to it All! is a apartment in Pleasant Pond, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Cozy~ON LIFT~Studio~Sugarloaf Views~Walk to it All!

Cozy~ON LIFT~Studio~Sugarloaf Views~Walk to it All! is a apartment in Pleasant Pond, 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, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,622.

From$232/night

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Sugarloaf Ski-In/Ski-Out Condo – Golf, Bike & Hike

Apartment, Pleasant Pond

Sugarloaf Ski-In/Ski-Out Condo – Golf, Bike & Hike is a apartment in Pleasant Pond, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Sugarloaf Ski-In/Ski-Out Condo – Golf, Bike & Hike

Sugarloaf Ski-In/Ski-Out Condo – Golf, Bike & Hike is a apartment in Pleasant Pond, 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, pool, hot tub, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,626.

From$232/night

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New Listing! Cozy Chalet 10-Minute Drive to Sugarloaf, Sleeps 9

Chalet, Pleasant Pond

New Listing! Cozy Chalet 10-Minute Drive to Sugarloaf, Sleeps 9 is a chalet in Pleasant Pond, with pet-friendly space, pool access, and room for a group. This stay gives travelers a…

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About New Listing! Cozy Chalet 10-Minute Drive to Sugarloaf, Sleeps 9

New Listing! Cozy Chalet 10-Minute Drive to Sugarloaf, Sleeps 9 is a chalet in Pleasant Pond, with pet-friendly space, pool 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, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,798.

From$257/night

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Vacation rentals with parking in Pleasant Pond, ME

Find vacation rentals that make arriving by car easier.

Post and beam cabin with queen size and bunk

Cabin, Pleasant Pond

Post and beam cabin with queen size and bunk is a cabin in Pleasant Pond, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Post and beam cabin with queen size and bunk

Post and beam cabin with queen size and bunk is a cabin in Pleasant Pond, 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 cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,077.

From$154/night

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Post and beam cabin with bunk beds

Cabin, Pleasant Pond

Post and beam cabin with bunk beds is a cabin in Pleasant Pond, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Post and beam cabin with bunk beds

Post and beam cabin with bunk beds is a cabin in Pleasant Pond, 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 cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,089.

From$156/night

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Gorgeous log cabin overlooking the Dead River just north of Berry's Store Rt 201

Cabin, Pleasant Pond

Gorgeous log cabin overlooking the Dead River just north of Berry's Store Rt 201 is a cabin in Pleasant Pond, with parking and kitchen access. This stay gives travelers a comfortable base…

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About Gorgeous log cabin overlooking the Dead River just north of Berry's Store Rt 201

Gorgeous log cabin overlooking the Dead River just north of Berry's Store Rt 201 is a cabin in Pleasant Pond, 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 cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,736.

From$391/night

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Cozy 2-bedroom chalet in lovely Carrabassett Valley

Chalet, Pleasant Pond

Cozy 2-bedroom chalet in lovely Carrabassett Valley is a chalet in Pleasant Pond, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Cozy 2-bedroom chalet in lovely Carrabassett Valley

Cozy 2-bedroom chalet in lovely Carrabassett Valley is a chalet in Pleasant Pond, 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 $1,182.

From$169/night

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Pet-friendly vacation rentals in Pleasant Pond, ME

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

PRITHAM HOUSE UNIT 3 GREENVILLE JCT>

Apartment, Pleasant Pond

PRITHAM HOUSE UNIT 3 GREENVILLE JCT> is a apartment in Pleasant Pond, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About PRITHAM HOUSE UNIT 3 GREENVILLE JCT>

PRITHAM HOUSE UNIT 3 GREENVILLE JCT> is a apartment in Pleasant Pond, 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 wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $825.

From$118/night

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Sugarloaf camp - ski/ outdoors rustic retreat

Cabin, Pleasant Pond

Sugarloaf camp - ski/ outdoors rustic retreat is a cabin in Pleasant Pond, with pet-friendly space, parking, and a quieter setting. This stay gives travelers a comfortable base for…

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About Sugarloaf camp - ski/ outdoors rustic retreat

Sugarloaf camp - ski/ outdoors rustic retreat is a cabin in Pleasant Pond, with pet-friendly space, parking, 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: free cancellation, pet friendly, pets friendly, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $908.

From$130/night

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UNIT 2 PRITHAM AVE GREENVILLE JCT., ME

Apartment, Pleasant Pond

UNIT 2 PRITHAM AVE GREENVILLE JCT., ME is a apartment in Pleasant Pond, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About UNIT 2 PRITHAM AVE GREENVILLE JCT., ME

UNIT 2 PRITHAM AVE GREENVILLE JCT., ME is a apartment in Pleasant Pond, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: hot tub, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,039.

From$148/night

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Mountain Lake Chalet

Holiday Home, Pleasant Pond

Mountain Lake Chalet is a holiday home in Pleasant Pond, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Mountain Lake Chalet

Mountain Lake Chalet is a holiday home in Pleasant Pond, 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 $1,098.

From$157/night

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Vacation rentals with a kitchen in Pleasant Pond, ME

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

Four season cabin near carrabassett river 5 min. from Sugarloaf mountain.

Cabin, Pleasant Pond

Four season cabin near carrabassett river 5 min. from Sugarloaf mountain. is a cabin in Pleasant Pond, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Four season cabin near carrabassett river 5 min. from Sugarloaf mountain.

Four season cabin near carrabassett river 5 min. from Sugarloaf mountain. is a cabin in Pleasant Pond, 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 cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,045.

From$149/night

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Air-Conditioned Hideaway Near Sugarloaf Mountain

Holiday Home, Pleasant Pond

Air-Conditioned Hideaway Near Sugarloaf Mountain is a holiday home in Pleasant Pond, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Air-Conditioned Hideaway Near Sugarloaf Mountain

Air-Conditioned Hideaway Near Sugarloaf Mountain is a holiday home in Pleasant Pond, 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 $1,371.

From$196/night

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Mountain View 3-bedroom apartment in Carrabassett Valley 10 minutes to Sugarloaf

Apartment, Pleasant Pond

Mountain View 3-bedroom apartment in Carrabassett Valley 10 minutes to Sugarloaf is a apartment in Pleasant Pond, with pet-friendly space, parking, and kitchen access. This stay gives…

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About Mountain View 3-bedroom apartment in Carrabassett Valley 10 minutes to Sugarloaf

Mountain View 3-bedroom apartment in Carrabassett Valley 10 minutes to Sugarloaf is a apartment in Pleasant Pond, 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 $1,419.

From$203/night

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Northwoods ATV, Hiking, Hunting Cabin with direct access to ITS-85 in Monson

Cabin, Pleasant Pond

Northwoods ATV, Hiking, Hunting Cabin with direct access to ITS-85 in Monson is a cabin in Pleasant Pond, with pet-friendly space and kitchen access. This stay gives travelers a comfortable…

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About Northwoods ATV, Hiking, Hunting Cabin with direct access to ITS-85 in Monson

Northwoods ATV, Hiking, Hunting Cabin with direct access to ITS-85 in Monson is a cabin in Pleasant Pond, 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 $1,467.

From$210/night

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Family-friendly vacation rentals in Pleasant Pond, ME

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

Charming 3-bedroom cottage in peaceful Solon with WiFi

Cottage, Pleasant Pond

Charming 3-bedroom cottage in peaceful Solon with WiFi is a cottage in Pleasant Pond, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Charming 3-bedroom cottage in peaceful Solon with WiFi

Charming 3-bedroom cottage in peaceful Solon with WiFi is a cottage in Pleasant Pond, 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 $1,188.

From$170/night

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Air-conditioned Hideaway Near Sugarloaf Mountain

Cottage, Pleasant Pond

Air-conditioned Hideaway Near Sugarloaf Mountain is a cottage in Pleasant Pond, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Air-conditioned Hideaway Near Sugarloaf Mountain

Air-conditioned Hideaway Near Sugarloaf Mountain is a cottage in Pleasant Pond, 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 $1,602.

From$175/night

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Updated retreat minutes from Sugarloaf

Condo, Pleasant Pond

Updated retreat minutes from Sugarloaf is a condo in Pleasant Pond, with kitchen access and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Updated retreat minutes from Sugarloaf

Updated retreat minutes from Sugarloaf is a condo in Pleasant Pond, with kitchen access 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: free cancellation, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,315.

From$188/night

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Sugarloaf Home, 2 bedrooms plus loft, 2 bathrooms - family & dog friendly

Holiday Home, Pleasant Pond

Sugarloaf Home, 2 bedrooms plus loft, 2 bathrooms - family & dog friendly is a holiday home in Pleasant Pond, with pet-friendly space and room for a group. This stay gives travelers a…

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About Sugarloaf Home, 2 bedrooms plus loft, 2 bathrooms - family & dog friendly

Sugarloaf Home, 2 bedrooms plus loft, 2 bathrooms - family & dog friendly is a holiday home in Pleasant Pond, 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: free cancellation, pet friendly, pets friendly, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,370.

From$196/night

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