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Middlefield Holiday Rentals

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50 rentals in Middlefield.
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Betty's Boat House, holiday rental in Middlefield

Betty's Boat House

2 bedrooms
1 bathroom
Sleeps 4
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Clarke's Landing, holiday rental in Middlefield

Clarke's Landing

3 bedrooms
3 bathrooms
Sleeps 8
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Moose Lodge At Clatter Ridge Farm, holiday rental in Middlefield

Moose Lodge At Clatter Ridge Farm

4 bedrooms
3 bathrooms
Sleeps 8
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Birdsong - Relaxation, Activities & Culture In Quaint Shoreline Town, holiday rental in Middlefield

Birdsong - Relaxation, Activities & Culture In Quaint Shoreline Town

1 bedroom
1 bathroom
Sleeps 2
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Newly Renovated Oceanfront Cottage On Joshua's Cove, Guilford CT, holiday rental in Middlefield

Newly Renovated Oceanfront Cottage On Joshua's Cove, Guilford CT

2 bedrooms
3 bathrooms
Sleeps 6
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Beautiful Beach House with Private Beach Access., holiday rental in Middlefield

Beautiful Beach House with Private Beach Access.

4 bedrooms
2 bathrooms
Sleeps 8
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Direct waterfront renovated cottage., holiday rental in Middlefield

Direct waterfront renovated cottage.

4 bedrooms
4 bathrooms
Sleeps 8
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Relax & Unwind at this Beautiful Lakefront Home in Connecticut, holiday rental in Middlefield

Relax & Unwind at this Beautiful Lakefront Home in Connecticut

3 bedrooms
2 bathrooms
Sleeps 6
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Branford-Pine Orchard Beach, holiday rental in Middlefield

Branford-Pine Orchard Beach

3 bedrooms
4 bathrooms
Sleeps 6
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Lake Front Home on the water, holiday rental in Middlefield

Lake Front Home on the water

5 bedrooms
4 bathrooms
Sleeps 14
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Two bedroom house with private beach and club within walking distance, holiday rental in Middlefield

Two bedroom house with private beach and club within walking distance

2 bedrooms
2 bathrooms
Sleeps 4
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Classic Cottage With Water Views Of Long Island Sound--Monthly rates available!, holiday rental in Middlefield

Classic Cottage With Water Views Of Long Island Sound--Monthly rates available!

5 bedrooms
3 bathrooms
Sleeps 8
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1 BR in Perfect Location to Yale, Downtown & Pizza, holiday rental in Middlefield

1 BR in Perfect Location to Yale, Downtown & Pizza

1 bedroom
1 bathroom
Sleeps 4
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Ennis Cottage- A Seaside Getaway!, holiday rental in Middlefield

Ennis Cottage- A Seaside Getaway!

1 bedroom
1 bathroom
Sleeps 4
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3/2 Private Lakefront Home 4 steps to the water-Kayaks, Canoe & Fire Pit, holiday rental in Middlefield

3/2 Private Lakefront Home 4 steps to the water-Kayaks, Canoe & Fire Pit

3 bedrooms
2 bathrooms
Sleeps 8
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Newly remodeled 1891 Queen Anne Victorian mansion, holiday rental in Middlefield

Newly remodeled 1891 Queen Anne Victorian mansion

1 bedroom
2 bathrooms
Sleeps 2
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Bright, cheery contemporary ranch style home, holiday rental in Middlefield

Bright, cheery contemporary ranch style home

3 bedrooms
2 bathrooms
Sleeps 4
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Private 2 bedroom near Yale, downtown, great restaurants and parks, holiday rental in Middlefield

Private 2 bedroom near Yale, downtown, great restaurants and parks

2 bedrooms
1 bathroom
Sleeps 4
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2 bedroom Apartment Brand New Listing Close to Beach & Downtown!, holiday rental in Middlefield

2 bedroom Apartment Brand New Listing Close to Beach & Downtown!

3 bedrooms
1 bathroom
Sleeps 4
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Private luxury waterfront home, holiday rental in Middlefield

Private luxury waterfront home

5 bedrooms
4 bathrooms
Sleeps 10
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Whole Apartment. Private. Walk to Yale and Downtown, holiday rental in Middlefield

Whole Apartment. Private. Walk to Yale and Downtown

3 bedrooms
1 bathroom
Sleeps 4
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Rustic Retreat near Bill Miller’s Castle available June 29th!!, holiday rental in Middlefield

Rustic Retreat near Bill Miller’s Castle available June 29th!!

4 bedrooms
3 bathrooms
Sleeps 10
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Amazing Waterfront Home, Private Beach,Hot Tub + Tennis/Beach Club, holiday rental in Middlefield

Amazing Waterfront Home, Private Beach,Hot Tub + Tennis/Beach Club

4 bedrooms
5 bathrooms
Sleeps 8
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Surrounded By Nature, holiday rental in Middlefield

Surrounded By Nature

4 bedrooms
4 bathrooms
Sleeps 10
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Peace Barn in the heart of the CT River Valley, holiday rental in Middlefield

Peace Barn in the heart of the CT River Valley

4 bedrooms
3 bathrooms
Sleeps 10
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Pet-Friendly Branford Home - 10Min Walk to Beach!, holiday rental in Middlefield

Pet-Friendly Branford Home - 10Min Walk to Beach!

3 bedrooms
1 bathroom
Sleeps 6
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Historic Mansion 1841, holiday rental in Middlefield

Historic Mansion 1841

5 bedrooms
3 bathrooms
Sleeps 7
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4 Room Apartment, holiday rental in Middlefield

4 Room Apartment

1 bedroom
1 bathroom
Sleeps 2
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Comfortable place to stay, holiday rental in Middlefield

Comfortable place to stay

1 bedroom
1 bathroom
Sleeps 2
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Money Island Home w/Deck, Kayak, Paddleboards, holiday rental in Middlefield

Money Island Home w/Deck, Kayak, Paddleboards

4 bedrooms
1 bathroom
Sleeps 8
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Waterfront New Haven Area Apt. on Joshua Cove, holiday rental in Middlefield

Waterfront New Haven Area Apt. on Joshua Cove

0 bedrooms
1 bathroom
Sleeps 4
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Elegant Meadowbrook Estate for Family Gatherings, Retreats and Special Events, holiday rental in Middlefield

Elegant Meadowbrook Estate for Family Gatherings, Retreats and Special Events

9 bedrooms
12 bathrooms
Sleeps 22
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Mind-blowing outdoorsman escape offering once- in- a lifetime experiences, holiday rental in Middlefield

Mind-blowing outdoorsman escape offering once- in- a lifetime experiences

1 bedroom
1 bathroom
Sleeps 4
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Charming summer home just steps from the beach!, holiday rental in Middlefield

Charming summer home just steps from the beach!

3 bedrooms
3 bathrooms
Sleeps 6
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Sunny and quiet bedroom near hospital and schools, holiday rental in Middlefield

Sunny and quiet bedroom near hospital and schools

1 bedroom
1 bathroom
Sleeps 2
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Luxurious 2BR - 2Bath W/ Gym | Downtown at Yale, holiday rental in Middlefield

Luxurious 2BR - 2Bath W/ Gym | Downtown at Yale

3 bedrooms
2 bathrooms
Sleeps 5
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Kasa | New Haven | Bright 1BD/1BA Apartment Near Yale, holiday rental in Middlefield

Kasa | New Haven | Bright 1BD/1BA Apartment Near Yale

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Kasa | New Haven | Cozy 1BD/1BA Apartment, holiday rental in Middlefield

Kasa | New Haven | Cozy 1BD/1BA Apartment

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Kasa | New Haven | Executive 1BD/1BA Apartment, holiday rental in Middlefield

Kasa | New Haven | Executive 1BD/1BA Apartment

1 bedroom
1 bathroom
Sleeps 4
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Kasa | New Haven | Convenient 1BD/1BA Near Yale, holiday rental in Middlefield

Kasa | New Haven | Convenient 1BD/1BA Near Yale

1 bedroom
1 bathroom
Sleeps 4
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Kasa | New Haven | Remote Work/Study Friendly 1BD/1BA Apartment, holiday rental in Middlefield

Kasa | New Haven | Remote Work/Study Friendly 1BD/1BA Apartment

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Kasa | New Haven | 1BD/1BA Apartment Minutes from Yale, holiday rental in Middlefield

Kasa | New Haven | 1BD/1BA Apartment Minutes from Yale

1 bedroom
1 bathroom
Sleeps 4
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Kasa | New Haven | Sunny 1BD/1BA Apartment, holiday rental in Middlefield

Kasa | New Haven | Sunny 1BD/1BA Apartment

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Kasa | New Haven | Charming 1BD/1BA Apartment, holiday rental in Middlefield

Kasa | New Haven | Charming 1BD/1BA Apartment

1 bedroom
1 bathroom
Sleeps 4
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Cabin Deck House - Formidable Cabin in Laurel Island, holiday rental in Middlefield

Cabin Deck House - Formidable Cabin in Laurel Island

4 bedrooms
1 bathroom
Sleeps 10
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Newly Remodeled 1BR Full Furnished Center of Town, holiday rental in Middlefield

Newly Remodeled 1BR Full Furnished Center of Town

1 bedroom
1 bathroom
Sleeps 2
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Cozy Fully Furnished 1BR, holiday rental in Middlefield

Cozy Fully Furnished 1BR

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Kasa New Haven | Self Check-In + Fast WiFi | Near Yale University, holiday rental in Middlefield

Kasa New Haven | Self Check-In + Fast WiFi | Near Yale University

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Kasa New Haven | Contactless Check-In + Walk to Campus | Near Yale University, holiday rental in Middlefield

Kasa New Haven | Contactless Check-In + Walk to Campus | Near Yale University

1 bedroom
1 bathroom
Sleeps 4
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Near Yale Cozy Niche Suite Studio, holiday rental in Middlefield

Near Yale Cozy Niche Suite Studio

0 bedrooms
1 bathroom
Sleeps 3
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