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Round Pond Holiday Rentals

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49 rentals in Round Pond.
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Beautiful Antique Waterfront Property On Round Pond Harbor - Sleeps 7, holiday rental in Round Pond

Beautiful Antique Waterfront Property On Round Pond Harbor - Sleeps 7

2 bedrooms
2 bathrooms
Sleeps 7
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The Barn at Round Pond, holiday rental in Round Pond

The Barn at Round Pond

1 bedroom
1 bathroom
Sleeps 2
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Coastal Home on Muscongus Bay, holiday rental in Round Pond

Coastal Home on Muscongus Bay

3 bedrooms
3 bathrooms
Sleeps 10
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New Listing! Tranquil Waterfront Hideaway w/ Modern Updates, holiday rental in Round Pond

New Listing! Tranquil Waterfront Hideaway w/ Modern Updates

2 bedrooms
2 bathrooms
Sleeps 6
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OceanView BonnieView, holiday rental in Round Pond

OceanView BonnieView

3 bedrooms
2 bathrooms
Sleeps 8
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Quiet and dog-friendly studio, walking distance to the harbor!, holiday rental in Round Pond

Quiet and dog-friendly studio, walking distance to the harbor!

0 bedrooms
1 bathroom
Sleeps 4
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Tranquil And Peaceful Vacation Getaway Just Waiting To Welcome You, holiday rental in Round Pond

Tranquil And Peaceful Vacation Getaway Just Waiting To Welcome You

2 bedrooms
1 bathroom
Sleeps 5
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Private Oceanfront Cottage, Private Sand Beach -Lighthouse one mile away, holiday rental in Round Pond

Private Oceanfront Cottage, Private Sand Beach -Lighthouse one mile away

2 bedrooms
1 bathroom
Sleeps 3
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Friendship Harbor Historic Home, holiday rental in Round Pond

Friendship Harbor Historic Home

5 bedrooms
2 bathrooms
Sleeps 8
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Stunning Property, Ocean Views, Beautifully Decorated, Fireplace, Chef's Kitchen, holiday rental in Round Pond

Stunning Property, Ocean Views, Beautifully Decorated, Fireplace, Chef's Kitchen

3 bedrooms
3 bathrooms
Sleeps 8
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Gorgeous Waterfront Property, holiday rental in Round Pond

Gorgeous Waterfront Property

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Your Windows To The Ocean, Lobstering Village, And Private Floating Dock!, holiday rental in Round Pond

Your Windows To The Ocean, Lobstering Village, And Private Floating Dock!

2 bedrooms
1 bathroom
Sleeps 6
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Secluded Lakefront Cottage on 5 acres. Very private, family friendly., holiday rental in Round Pond

Secluded Lakefront Cottage on 5 acres. Very private, family friendly.

3 bedrooms
2 bathrooms
Sleeps 6
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Beautifully Renovated Historic Inn, holiday rental in Round Pond

Beautifully Renovated Historic Inn

6 bedrooms
3 bathrooms
Sleeps 14
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Seaworthy- A Perfect Maine Coast Location, holiday rental in Round Pond

Seaworthy- A Perfect Maine Coast Location

3 bedrooms
2 bathrooms
Sleeps 6
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Cozy Cottage with Freshwater Frontage & Saltwater View, holiday rental in Round Pond

Cozy Cottage with Freshwater Frontage & Saltwater View

2 bedrooms
1 bathroom
Sleeps 4
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The Gallery Apartment in Damariscotta, Maine for stays of 3 or more nights, holiday rental in Round Pond

The Gallery Apartment in Damariscotta, Maine for stays of 3 or more nights

1 bedroom
1 bathroom
Sleeps 3
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Maine Coast House with Spectacular Ocean Views and Sandy Beach for Swimming, holiday rental in Round Pond

Maine Coast House with Spectacular Ocean Views and Sandy Beach for Swimming

3 bedrooms
2 bathrooms
Sleeps 6
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Slow Down & Go Back in Time-Relax Completely in Our Maine Home, holiday rental in Round Pond

Slow Down & Go Back in Time-Relax Completely in Our Maine Home

2 bedrooms
1 bathroom
Sleeps 6
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Spend the Coming Summer in a Private Home in Round Pond, Maine, holiday rental in Round Pond

Spend the Coming Summer in a Private Home in Round Pond, Maine

2 bedrooms
2 bathrooms
Sleeps 4
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Charming Home W/Harbor View: Walk to Resturants, Shops & Beach, holiday rental in Round Pond

Charming Home W/Harbor View: Walk to Resturants, Shops & Beach

3 bedrooms
2 bathrooms
Sleeps 6
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Charming Woodsy Cottage - Ocean View with Monhegan Island, holiday rental in Round Pond

Charming Woodsy Cottage - Ocean View with Monhegan Island

3 bedrooms
1 bathroom
Sleeps 5
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Contemporary Cottage With Spectacular Ocean Views And Access, holiday rental in Round Pond

Contemporary Cottage With Spectacular Ocean Views And Access

2 bedrooms
2 bathrooms
Sleeps 5
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Maine Oceanfront Cottage - newly built in 2019, holiday rental in Round Pond

Maine Oceanfront Cottage - newly built in 2019

4 bedrooms
2 bathrooms
Sleeps 6
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Oar Island, holiday rental in Round Pond

Oar Island

3 bedrooms
1 bathroom
Sleeps 8
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Finch Cottage, holiday rental in Round Pond

Finch Cottage

2 bedrooms
2 bathrooms
Sleeps 4
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The Loft Guest Cottage, holiday rental in Round Pond

The Loft Guest Cottage

2 bedrooms
1 bathroom
Sleeps 4
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Shearwater a uniquely charming Maine cottage near the rocky coast, holiday rental in Round Pond

Shearwater a uniquely charming Maine cottage near the rocky coast

4 bedrooms
4 bathrooms
Sleeps 8
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Large, Private Family Home Recently Renovated, holiday rental in Round Pond

Large, Private Family Home Recently Renovated

3 bedrooms
2 bathrooms
Sleeps 6
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Maine Bed & Boat, NEBI, holiday rental in Round Pond

Maine Bed & Boat, NEBI

2 bedrooms
2 bathrooms
Sleeps 4
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South Bristol Boathouse, holiday rental in Round Pond

South Bristol Boathouse

2 bedrooms
2 bathrooms
Sleeps 4
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Classic Retro Cottage, holiday rental in Round Pond

Classic Retro Cottage

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Private Lake Island with Million Dollar View, holiday rental in Round Pond

Private Lake Island with Million Dollar View

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Dalton Cottage on Coast of Maine with Spectacular Views & Crashing Surf, holiday rental in Round Pond

Dalton Cottage on Coast of Maine with Spectacular Views & Crashing Surf

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Your Maine Dream Vacation Awaits, holiday rental in Round Pond

Your Maine Dream Vacation Awaits

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Nestled in the Trees with Ocean Views, holiday rental in Round Pond

Nestled in the Trees with Ocean Views

2 bedrooms
1 bathroom
Sleeps 4
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Charming oceanfront cottage, holiday rental in Round Pond

Charming oceanfront cottage

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Open Floor-plan Home near Harbor, Beach and Lighthouse, holiday rental in Round Pond

Open Floor-plan Home near Harbor, Beach and Lighthouse

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Former B&B - now the whole home is available as a weekly rental, holiday rental in Round Pond

Former B&B - now the whole home is available as a weekly rental

5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Maine Island Lodge, holiday rental in Round Pond

Maine Island Lodge

7 bedrooms
6 bathrooms
Sleeps 18
Match: Sleeps
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Lakefront cottage w/dock & island in Biscay Pond, screened porch, holiday rental in Round Pond

Lakefront cottage w/dock & island in Biscay Pond, screened porch

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Romantic Oceanfront Camp for Two, holiday rental in Round Pond

Romantic Oceanfront Camp for Two

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Remarkable Four Gable House Overlooking Friendship Harbor, holiday rental in Round Pond

Remarkable Four Gable House Overlooking Friendship Harbor

8 bedrooms
6 bathrooms
Sleeps 18
Match: Sleeps
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Damariscotta waterfront home, holiday rental in Round Pond

Damariscotta waterfront home

4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Light Filled, Woodsy Views, Atlantic Ocean Nearby - Classic Mid-Coast Cottage, holiday rental in Round Pond

Light Filled, Woodsy Views, Atlantic Ocean Nearby - Classic Mid-Coast Cottage

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Quintessential Maine! Green Gables Oceanfront Cottage w/ Secluded Beach, holiday rental in Round Pond

Quintessential Maine! Green Gables Oceanfront Cottage w/ Secluded Beach

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Overlooking the Ocean with Large Porch, holiday rental in Round Pond

Overlooking the Ocean with Large Porch

5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Charming Cottage just a short walk to Pemaquid Beach!, holiday rental in Round Pond

Charming Cottage just a short walk to Pemaquid Beach!

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Spacious home on the river w/ outdoor firepit & views of the water!, holiday rental in Round Pond

Spacious home on the river w/ outdoor firepit & views of the water!

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cozy Cottage   with spectacular salt water  view / 4 Kayaks available, holiday rental in Round Pond

Cozy Cottage with spectacular salt water view / 4 Kayaks available

1 bedroom
1 bathroom
Sleeps 1
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