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Holiday Homes in Waldoboro

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48 rentals in Waldoboro.
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Charming Pet Friendly MidCoast Maine Coach House - Great WiFi, Clean & Cozy, holiday rental in Waldoboro

Charming Pet Friendly MidCoast Maine Coach House - Great WiFi, Clean & Cozy

2 bedrooms
1 bathroom
Sleeps 4
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Waterfront Property w. Stunning Views, Designer-Renovated 1884 Cape on 15 Acres, holiday rental in Waldoboro

Waterfront Property w. Stunning Views, Designer-Renovated 1884 Cape on 15 Acres

3 bedrooms
2 bathrooms
Sleeps 6
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Former Sea Captains' 1850s Greek Revival home minutes to town and boat launch, holiday rental in Waldoboro

Former Sea Captains' 1850s Greek Revival home minutes to town and boat launch

5 bedrooms
4 bathrooms
Sleeps 9
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Water Front post and beam guest house 'Thyme & Tide', on Muscongus Bay., holiday rental in Waldoboro

Water Front post and beam guest house 'Thyme & Tide', on Muscongus Bay.

3 bedrooms
4 bathrooms
Sleeps 6
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Remodeled waterfront home with a wrap-around deck, water views & beach access!, holiday rental in Waldoboro

Remodeled waterfront home with a wrap-around deck, water views & beach access!

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Come and relax in Mid Coast Maine. We are child and pet friendly., holiday rental in Waldoboro

Come and relax in Mid Coast Maine. We are child and pet friendly.

3 bedrooms
2 bathrooms
Sleeps 8
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Private riverfront retreat w/ foosball & a firepit, overlooks a nature preserve!, holiday rental in Waldoboro

Private riverfront retreat w/ foosball & a firepit, overlooks a nature preserve!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Farm House located on the Medomak River, Oceanfront, holiday rental in Waldoboro

Beautiful Farm House located on the Medomak River, Oceanfront

4 bedrooms
3 bathrooms
Sleeps 6
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'Blueberry Cottage' on Scenic Back River Cove, holiday rental in Waldoboro

'Blueberry Cottage' on Scenic Back River Cove

2 bedrooms
1 bathroom
Sleeps 5
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Lovely 'Raspberry Cottage' w/Rowboat on Back Cove!, holiday rental in Waldoboro

Lovely 'Raspberry Cottage' w/Rowboat on Back Cove!

2 bedrooms
1 bathroom
Sleeps 5
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Historic Waldoboro House Near Lakes, Boating, Etc!, holiday rental in Waldoboro

Historic Waldoboro House Near Lakes, Boating, Etc!

3 bedrooms
2 bathrooms
Sleeps 6
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Friendship Harbor Historic Home, holiday rental in Waldoboro

Friendship Harbor Historic Home

5 bedrooms
2 bathrooms
Sleeps 8
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1820's artist owned cape on 50+ acres near town and mid coast activities, holiday rental in Waldoboro

1820's artist owned cape on 50+ acres near town and mid coast activities

4 bedrooms
1 bathroom
Sleeps 6
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The Pink Cottage on beautiful Damariscotta Lake., holiday rental in Waldoboro

The Pink Cottage on beautiful Damariscotta Lake.

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

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 Waldoboro

Beautifully Renovated Historic Inn

6 bedrooms
3 bathrooms
Sleeps 14
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Real Maine Lake Camp Double Occupancy No Children No Pets, holiday rental in Waldoboro

Real Maine Lake Camp Double Occupancy No Children No Pets

2 bedrooms
1 bathroom
Sleeps 2
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Lakefront getaway with panaromic views of Damariscotta Lake inside and out!, holiday rental in Waldoboro

Lakefront getaway with panaromic views of Damariscotta Lake inside and out!

3 bedrooms
1 bathroom
Sleeps 6
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Beautiful Sunsets on Damariscotta Lake, holiday rental in Waldoboro

Beautiful Sunsets on Damariscotta Lake

2 bedrooms
1 bathroom
Sleeps 4
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Riverfront, Midcoast Maine, holiday rental in Waldoboro

Riverfront, Midcoast Maine

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Maine Summer Camp on Damariscotta Lake in the Midcoast, holiday rental in Waldoboro

Maine Summer Camp on Damariscotta Lake in the Midcoast

2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Lakefront mobile home near dock with grill, picnic area, & great view, holiday rental in Waldoboro

Lakefront mobile home near dock with grill, picnic area, & great view

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Lovely Shipbuilder Victorian home peaceful w/ view of Damariscotta River, holiday rental in Waldoboro

Lovely Shipbuilder Victorian home peaceful w/ view of Damariscotta River

4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Maine Oceanfront Cottage - newly built in 2019, holiday rental in Waldoboro

Maine Oceanfront Cottage - newly built in 2019

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

Oar Island

3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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“STEP BACK IN TIME” 1880’ charmer, holiday rental in Waldoboro

“STEP BACK IN TIME” 1880’ charmer

2 bedrooms
1 bathroom
Sleeps 4
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Private Lake Island with Million Dollar View, holiday rental in Waldoboro

Private Lake Island with Million Dollar View

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Charming cottage in wooded area, an open floor plan, overlooking tidal water, holiday rental in Waldoboro

Charming cottage in wooded area, an open floor plan, overlooking tidal water

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Your Maine Dream Vacation Awaits, holiday rental in Waldoboro

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 Waldoboro

Nestled in the Trees with Ocean Views

2 bedrooms
1 bathroom
Sleeps 4
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lakefront hideaway, holiday rental in Waldoboro

lakefront hideaway

3 bedrooms
2 bathrooms
Sleeps 7
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Charming oceanfront cottage, holiday rental in Waldoboro

Charming oceanfront cottage

2 bedrooms
1 bathroom
Sleeps 4
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Maine Island Lodge, holiday rental in Waldoboro

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 Waldoboro

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

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Rustic Lakeside Lodge and Four Cabins-13 bedrooms, holiday rental in Waldoboro

Rustic Lakeside Lodge and Four Cabins-13 bedrooms

10 bedrooms
9 bathrooms
Sleeps 26
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Lake Front Housekeeping Cottage, holiday rental in Waldoboro

Lake Front Housekeeping Cottage

2 bedrooms
1 bathroom
Sleeps 4
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Lake Front Housekeeping Cottage B, holiday rental in Waldoboro

Lake Front Housekeeping Cottage B

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Remarkable Four Gable House Overlooking Friendship Harbor, holiday rental in Waldoboro

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 Waldoboro

Damariscotta waterfront home

4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Quintessential Maine! Green Gables Oceanfront Cottage w/ Secluded Beach, holiday rental in Waldoboro

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 Waldoboro

Overlooking the Ocean with Large Porch

5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Tentrr Signature Site - Private Waterside Retreat, holiday rental in Waldoboro

Tentrr Signature Site - Private Waterside Retreat

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Pond Site Paradise, holiday rental in Waldoboro

Tentrr Signature Site - Pond Site Paradise

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Reunion Grove Farm - Relax with us!, holiday rental in Waldoboro

Reunion Grove Farm - Relax with us!

2 bedrooms
1 bathroom
Sleeps 6
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Beautiful Home on Pemaquid Lake, holiday rental in Waldoboro

Beautiful Home on Pemaquid Lake

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Spacious lake house with dock and sandy beach, holiday rental in Waldoboro

Spacious lake house with dock and sandy beach

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Stunning Post and Beam, offering waterfront privacy, holiday rental in Waldoboro

Stunning Post and Beam, offering waterfront privacy

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Spacious Lakefront Home on Lush 5-Acre Lot with Sunny Deck & Private Dock, holiday rental in Waldoboro

Spacious Lakefront Home on Lush 5-Acre Lot with Sunny Deck & Private Dock

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Little Gray Cottage On The Lake, holiday rental in Waldoboro

Little Gray Cottage On The Lake

2 bedrooms
1 bathroom
Sleeps 1
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Cozy Cottage   with spectacular salt water  view / 4 Kayaks available, holiday rental in Waldoboro

Cozy Cottage with spectacular salt water view / 4 Kayaks available

1 bedroom
1 bathroom
Sleeps 1
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